JP2001081077A - Ethylene derivative and pest controlling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound comprising a specific ethylene derivative, having high safety, exhibiting an excellent pest controlling activity and an excellent preventing activity for the attachment of aquatic organisms, having low toxicity and low residual properties and useful as an insecticide and an acaricide. SOLUTION: This compound is represented by formula I [Q is a group represented by formula II W is a group represented by formula III [X is represented by N-X1 (X1 is a 1-10C alkyl or the like) or the like; Y is H, a 1-10C alkyl or the like] or the like; R is a halogen, a 1-10C alkyl or the like; p is O-2) or the like; A is a group represented by formula IV (G is a halogen, a 1-6C haloalkyl or the like; m is 0-3) or the like; B is H, a 1-4C alkyl or the like], e.g. 2-[3-(2-aza-2-methoxy-1-methylvinyl)pyrazolyl]-2-cyano-1-(1,3,4- trimethylpyrazol-5-yl)vinyl 2,2-dimethylpropanoate. The compound represented by formula I is obtained by reacting an acetonitrile derivative with acid chlorides, etc., and further reacting the resultant compound with alkyl halides. The reactional temperature is preferably -30 to +200 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel ethylene derivative and a pesticide and an underwater biofouling inhibitor comprising the derivative as an active ingredient. Pesticides in the present invention, insecticides, acaricides, nematicides, herbicides, fungicides and the like, especially agricultural and horticultural, livestock,
It is a pesticide in the field of hygiene. Underwater organism antifouling agents include fishing nets, ship bottoms, buoys and other underwater facilities, marine structures, condenser cooling water systems for thermal or nuclear power plants, and water intake channels for heat exchanger cooling water in the chemical industry. It is an agent for preventing harmful aquatic organisms such as shellfish and algae from adhering to underwater structures or reservoirs.

[0002]

2. Description of the Related Art Acrylonitrile derivatives as pesticides are described in WO-97 / 40009.

[0003]

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

[0004] Further, in order to prevent the adhesion and propagation of aquatic organisms in the sea and freshwater, antifouling paints containing organic tin compounds such as bistributyltin oxide and copper compounds such as copper sulfate and cuprous oxide have been used. I have. However, although the organotin compounds are effective in preventing the adhesion of aquatic organisms, they are highly toxic, and especially accumulate in fish and shellfish in the body, and are subject to environmental pollution. Copper compounds are widely used in antifouling paints for intake channels and ship bottoms, but contain copper, which is a heavy metal like tin compounds. There is a demand for an underwater biofouling inhibitor which does not affect the ecosystem and has less secondary pollution, rather than being an inhibitor.

[0005]

In order to solve the above-mentioned problems, the present inventors have demonstrated excellent pest control activity at a low dose and against non-target organisms such as mammals, fish and beneficial insects. As a result of continuing research to develop pesticides and underwater biofouling inhibitors with little adverse effect, the following compounds were found to be highly safe and have excellent pest control activity and underwater biofouling prevention activity. Completed the invention.

That is, the present invention provides the following [1] to [19]
And a pesticide and an underwater biofouling inhibitor containing the derivative as an active ingredient.

[1] Equation (1):

[0008]

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[Wherein Q is

[0010]

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[0011]

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[0012]

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[0013]

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And A is

[0015]

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[0016]

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[0017]

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Wherein B is H, C ₁ -C ₄ alkyl, C
₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl alkyl, C
_{H 3 SCH 2, CH 3 OC} 2 H 4 OCH 2, C 1 ~C 4 alkyl, halogen or C ₁ -C ₄ substituted in phenyl substituted with halogen or C ₁ -C ₄ alkyl
C ₁ -C ₄ alkyl substituted with benzoyl optionally substituted with alkyl, tetrahydropyranyl, (C
_{H 3) 3 Si, C 1} ~C 4 alkylsulfonyl, halogen or C ₁ -C ₄ phenyl sulfonyl optionally substituted by _{alkyl, -SO 2 CF 3, C 1} ~C 4 monoalkylamino aminosulfonyl, C ₂ -C ₈ dialkylaminosulfonyl, phenylaminosulfonyl, C ₂ -C ₅ mono alkylaminothiocarbonyl, C ₃ -C ₉ dialkylaminothiocarbonyl, C ₂ -C ₅ cyanoalkyl, C ₃ -C ₉ alkoxycarbonylalkyl, - ^{C (= O) T 1,} -P (=
^{O) T 2 T 3, -P} (= S) T 2 T 3, an alkali metal atom,
An alkaline earth metal atom or NHT ⁴ T ⁵ T ⁶ and W
Is

[0019]

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Wherein R is halogen, C₁~ C_TenAl
Kill, halogen or C₁~ C_FourSubstituted with alkyl
Optionally substituted phenyl substituted C₁~ C_FourAlkyl, C
_Two~ C₆Alkenyl, C_Two~ C₆Alkynyl, C₁~ C₆C
Lower alkyl, C_Two~ C₆Haloalkenyl, C_Two~ C₆Haloa
Lucinyl, C_Three~ C₆Halocycloalkyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy, C_Two
~ C₆Alkynyloxy, C₁~ C_FourHaloalkoxy, C_Two
~ C₆Haloalkenyloxy, C_Two~ C₆Haloalkynyl
Oxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAl
Killsulfinyl, C₁~ C_FourAlkylsulfonyl, C_Two
~ C₆Alkenylsulfenyl, C_Two~ C₆Alkenyls
Rufinil, C_Two~ C₆Alkenylsulfonyl, C_Two~ C₆
Alkynylsulfenyl, C_Two~ C₆Alkynyl sulf
Inil, C_Two~ C₆Alkynylsulfonyl, C₁~ C_FourHalo
Alkylsulfenyl, C₁~ C_FourHaloalkyl sulfy
Nil, C₁~ C_FourHaloalkylsulfonyl, C_Two~ C₆Halo
Alkenylsulfenyl, C_Two~ C₆Haloalkenylsul
Finil, C_Two~ C₆Haloalkenylsulfonyl, C_Two~
C₆Haloalkynylsulfenyl, C_Two~ C₆Haloalk
Nilsulfinyl, C_Two~ C₆Haloalkynylsulfoni
Le, NO_Two, CN, -NU¹U^Two, Phenoxy, OH, nafti
Le, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourAlkoki
Sialkyl, C_Two~ C_FourAlkylcarbonyl, C_Two~ C_FiveA
Alkylcarbonyloxy, C_Two~ C_FiveHaloalkylcarbo
Nyloxy, benzoyl optionally substituted with Z, Z
Optionally substituted phenyl, optionally substituted with Z
Good pyridyl, thienyl optionally substituted by Z or
Is -N = CT⁷T⁸Or adjacent R or
R^TwoTogether with a 5-membered ring formed by an alkylene group, 6
A 7-membered ring, a 7-membered ring or an 8-membered ring,^TwoIs H, C₁~ C_Ten
Alkyl, halogen or C₁~ C_FourSubstituted with alkyl
Optionally substituted phenyl substituted C₁~ C_FourArchi
Le, C_Two~ C₆Alkenyl, C_Two~ C₆Alkynyl, C₁
~ C₆Haloalkyl, C₁~ C_ThreeSubstituted with alkyl
May be C_Three~ C₆Cycloalkyl, naphthyl, C_Two~ C₇
Alkoxycarbonyl, C_Two~ C_FourAlkoxyalkyl,
C_Two~ C_FourAlkylcarbonyl, which may be substituted with Z
Benzoyl, phenyl optionally substituted with Z, Z
Optionally substituted pyridyl, optionally substituted with Z
Good thienyl or -N = CT⁷T⁸Or
5 members formed by an alkylene group with adjacent R
A ring, a 6-membered ring, a 7-membered ring or an 8-membered ring,^ThreeIs H
Is C₁~ C_TenG is halogen, C₁~ C
_TenAlkyl, C₁~ C₆Haloalkyl, C₁~ C₆Alkoki
Si, C_Two~ C₆Alkenyloxy, C_Two~ C₆Alkynyluo
Kissi, C₁~ C_FourHaloalkoxy, C_Two~ C₆Haloalkene
Luoxy, C_Two~ C₆Haloalkynyloxy, C ₁~ C_FourA
Rukylsulfenyl, C₁~ C_FourAlkylsulfinyl,
C₁~ C_FourAlkylsulfonyl, C_Two~ C₆Alkenyl sulf
Phenyl, C_Two~ C₆Alkenylsulfinyl, C_Two~ C₆
Alkenylsulfonyl, C_Two~ C₆Alkynylsulfeni
Le, C_Two~ C₆Alkynylsulfinyl, C_Two~ C₆Archi
Nylsulfonyl, C₁~ C_FourHaloalkylsulfenyl,
C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloal
Killsulfonyl, C_Two~ C₆Haloalkenylsulfeni
Le, C_Two~ C₆Haloalkenylsulfinyl, C_Two~ C₆C
Loalkenylsulfonyl, C_Two~ C₆Haloalkynylsul
Phenyl, C_Two~ C₆Haloalkynylsulfinyl, C_Two
~ C₆Haloalkynylsulfonyl, NO_Two, CN, -NU
¹U^Two, OH, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_Four
Alkoxyalkyl, C_Two~ C_FiveAlkylcarbonyl, C
_Two~ C_FiveHaloalkylcarbonyl, C_Two~ C_FiveAlkyl cal
Bonyloxy, C_Two~ C_FiveHaloalkylcarbonyloxy
Si, C_Three~ C₇Dialkylaminocarbonyloxy, Z
Optionally substituted phenyl or -N = CT⁷T⁸so
Existing or adjacent G or G¹With alkylene
5-, 6-, 7- or 8-membered ring formed by a group
Is a member ring and G¹Is H, C₁~ C_TenAlkyl and halogen
Or C₁~ C_FourPhenyl optionally substituted with alkyl
Replaced with₁~ C_FourAlkyl, C_Two~ C₆Alkene
Le, C _Two~ C₆Alkynyl, C₁~ C₆Haloalkyl, C₁
~ C_ThreeC optionally substituted with alkyl_Three~ C₆Cyclo
Alkyl, naphthyl, C_Two~ C₇Alkoxycarbonyl,
C _Two~ C_FourAlkoxyalkyl, C_Two~ C_FourAlkyl carb
Nil, benzoyl optionally substituted with Z, substituted with Z
Phenyl which may be substituted,
Lysyl, thienyl optionally substituted with Z or -N
= CT⁷T⁸Or with an adjacent G
5-membered ring, 6-membered ring, 7-membered ring or
Is an 8-membered ring, and X is N-X¹, CH-X¹, C- (X¹)_Two, O
Or S and X¹Is C₁~ C_TenAlkyl, C_Two~ C₆A
Lucenyl, C_Two~ C₆Alkynyl, C₁~ C₆Haloalk
Le, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy,
C_Two~ C₆Alkynyloxy, C₁~ C_FourHaloalkoxy,
C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Halo alkini
Luoxy, C₁~ C_FourA which may be substituted with alkyl;
Riloxy, C₁~ C_FourAlkylsulfenyl, C₁~ C_Four
Alkylsulfinyl, C ₁~ C_FourAlkylsulfonyl,
C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Shiku
Low alkyl, NO_Two, CN, -NU¹U^Two, OH, C_Two~ C₇A
Lucoxycarbonyl, C_Two~ C_FourAlkoxyalkyl, C
_Two~ C_FourAlkylcarbonyl, C_Two~ C_FiveHaloalkylcal
Bonil, C_Two~ C_FiveAlkylcarbonyloxy, C_Two~ C_Five
Haloalkylcarbonyloxy, C_Three~ C₇Dialkylur
Minocarbonyloxy, morpholinyl, piperidyl, Z
Benzoyl optionally substituted with
Phenyl, phenoxy optionally substituted with Z
Pyridyl optionally substituted by Z or Z (provided that
X is CH-X¹Or C- (X¹)_TwoX¹Is C₁~ C_Ten
Alkyl, C_Two~ C₆Alkenyl and C₁~ C₆Haloalk
Not. Also, X¹When two or more are the same or
May be different. ), Y is H, C₁~ C_TenAlkyl, C_Two
~ C₆Alkenyl, C_Two~ C₆Alkynyl, C₁~ C₆Halo
Alkyl, C₁~ C₆Alkoxy, C_Two~ C₆Alkenylo
Kissi, C_Two~ C ₆Alkynyloxy, C₁~ C_FourHalo alco
Kissi, C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Haloa
Lucinyloxy, C₁~ C_FourEven if substituted with alkyl
Good allyloxy, C₁~ C_FourAlkylsulfenyl, C
₁~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfo
Nil, C₁~ C_ThreeC optionally substituted with alkyl_Three~
C₆Cycloalkyl, CN, -NU¹U^Two, -C (= O) T¹,
C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FiveMonoalkylur
Minothiocarbonyl, C_Three~ C₉Dialkylaminothioca
Rubonil, C_Two~ C₆Alkylthiocarbonyl, morpholy
Pyrazolyl optionally substituted with nil, piperidyl and Z
I, imidazolyl optionally substituted with Z, substituted with Z
Pyrazolinyl which may be optionally substituted by Z
Pyridyl optionally substituted with phenyl or Z
Is or R or R^TwoTogether with an alkylene group
A 5-, 6-, 7- or 8-membered ring formed by
(However, when X is O, Y is alkyl or alkoxy.
Not. ), X^TwoIs S, O, NR^FourOr CH_Two(But
Then X^TwoWhen two or more are the same or different
No. ), X^ThreeIs S, O or NR^FourAnd R^FourIs H, C₁
~ C_TenAlkyl, halogen or C₁~ C_FourWith alkyl
C substituted with optionally substituted phenyl₁~ C_FourA
Luquil, C_Two~ C₆Alkenyl, C_Two~ C₆Alkynyl,
C₁~ C₆Haloalkyl, C₁~ C_ThreeSubstituted with alkyl
May be C_Three~ C₆Cycloalkyl, naphthyl, C_Two~
C₇Alkoxycarbonyl, C_Two~ C_FourAlkoxyalkyl
Le, C_Two~ C_FourAlkylcarbonyl, substituted with Z
Benzoyl, phenyl optionally substituted by Z
, Pyridyl optionally substituted with Z, substituted with Z
Optionally thienyl or -N = CT⁷T⁸And Z
Is halogen, C₁~ C_FourAlkyl, C₁~ C_FourHaloalk
Le, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C
₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulf
Inil, C₁~ C_FourAlkylsulfonyl, C_Two~ C_FiveArche
Nilsulfenyl, C_Two~ C_FiveAlkenylsulfinyl,
C_Two~ C_FiveAlkenylsulfonyl, C₁~ C_FourHaloalkyl
Sulfenyl, C₁~ C_FourHaloalkylsulfinyl, C
₁~ C _FourHaloalkylsulfonyl, NO_Two, CN, CH
O, OH, -NU¹U^Two, Phenyl, phenoxy and C_Two~ C_Five
1 to 5 members selected from alkoxycarbonyl
Substituents which may be different from each other,¹Is C₁~ C₂₀
Alkyl, C_Two~ C₆Alkenyl, C₁~ C₆Haloalk
Le, C ₁~ C_FourAlkoxy-C₁~ C_FourAlkyl, C_Three~ C₆
Halocycloalkyl, halogen or C₁~ C_FourArchi
Substituted with phenyl optionally substituted with₁~
C_FourAlkyl, C₁~ C_ThreeMay be substituted with alkyl
C_Three~ C₆Cycloalkyl, halogen or C₁~ C_Four
Substituted with phenyl optionally substituted with alkyl
Cycloalkyl, halogen or C₁~ C_FourWith alkyl
Optionally substituted phenyl and C₁~ C_FourAlkyl
Substituted cyclopropyl, halogen or C₁~ C_FourA
With phenyl and halogen optionally substituted with alkoxy
Replaced C_Three~ C_FourSubstituted with cycloalkyl group and halogen
C that may be_Two~ C_FourAlkenyl and C₁~ C_FourArchi
Substituted with a cyclopropyl group, halogen or C
₁~ C_FourSubstituted with phenyl which may be substituted with an alkyl group.
Transformed C_Two~ C_FourAlkenyl, C₁~ C₁₂Alkoxy,
C₁~ C_FourHaloalkoxy, C_Two~ C_FiveAlkenyloxy,
C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Shiku
Lower alkoxy, benzyloxy, C_Two~ C_FiveAlkoxyka
Rubonil, -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,
Heterocyclic groups are thienyl, furyl, pyrrolyl, oxazoly
, Isoxazolyl, thiazolyl, isothiazolyl,
Lazolyl, imidazolyl, 1,3,4-oxadiazoli
1,2,4-oxadiazolyl, 1,3,4-thia
Diazolyl, 1,2,4-thiadiazolyl, 1,2,4
-Triazolyl, 1,2,3-thiadiazolyl, 1,
2,3-triazolyl, 1,2,3,4-tetrazoli
, Pyridyl, pyrimidinyl, pyrazinyl, pyridazini
1,3,5-triazinyl, 1,2,4-triazi
Nil, pyrazolinyl, imidazolinyl, oxazolini
, Isoxazolinyl, thiazolinyl and 3 (2H)-
Selected from pyridazinone. ) And T^TwoAnd T^Three
Is independently OH, phenyl, C₁~ C₆Alkyl,
C₁~ C₆Alkoxy or C₁~ C_FourAlkylsulfeni
And T^Four, T^FiveAnd T⁶Is independently H, C₁~
C₆Alkyl, C₁~ C₆Alkenyl, C₁~ C_ThreeAlkyl
C optionally substituted with a group_Three~ C₆Up to cycloalkyl groups
Or benzyl or T^Four, T^FiveAnd T⁶Horse
The other two are acids together with the nitrogen atom to which each is attached.
May contain elemental, nitrogen or sulfur atoms
To form a 5-, 6-, 7- or 8-membered ring group
And T⁷And T⁸Is each independently H, phenyl,
Benzyl or C₁~ C₆Alkyl or T
⁷ _{And T} ⁸Ring with the carbon atom to which it is bonded, 6-membered
May form a ring, a 7-membered ring or an 8-membered ring,¹And U
^TwoIs independently H, C₁~ C₆Alkyl, C_Two~ C_FiveA
Alkylcarbonyl, phenyl or benzyl, or
Or U¹And U^Two5 members with the carbon atom to which they are attached
May form a ring, a 6-membered ring, a 7-membered ring or an 8-membered ring,
Represents the number of methylene, and is 0, 1, 2 or 3;
m represents the number of substituents, and is 0, 1, 2 or 3;
n represents the number of substituents, and is 0, 1, 2, 3, or 4.
And p represents the number of substituents, and is 0, 1 or 2,
q represents the number of substituents, and is 0 or 1 (provided that m, n and
And when p represents an integer of 2 or more, the substituents are the same
They may be different from each other. )] Ethylene derivative
body.

[2] Q is

[0022]

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[0023]

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[0024]

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[0025]

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Where B is H, C₁~ C_FourAlkyl, C
₁~ C_FourHaloalkyl, C_Two~ C_FourAlkoxyalkyl, C
H_ThreeOC_TwoH_FourOCH_Two, C₁~ C_FourAlkylsulfonyl, ha
Logen or C₁May be substituted with -C4 alkyl
Phenylsulfonyl, -SO_TwoCF_Three, C_Two~ C₈Gials
Killaminosulfonyl, C_Two~ C₉Dialkylaminothio
Carbonyl, C_Three~ C₉Alkoxycarbonylalkyl,
-C (= O) T¹, -P (= O) T^TwoT^Three, -P (= S)
T^TwoT^Three, Alkali metal atoms, alkaline earth metal atoms or
Is NHT^FourT^FiveT⁶And R¹Is H, halogen, C₁~ C
_TenAlkyl, halogen or C₁~ C_FourSubstitute with alkyl
Optionally substituted phenyl substituted C₁~ C_FourArchi
Le, C_Two~ C₆Alkenyl, C_Two~ C₆Alkynyl, C₁
~ C₆Haloalkyl, C_Two~ C₆Haloalkenyl, C_Two~ C
₆Haloalkynyl, C_Three~ C₆Halocycloalkyl, C₁~
C_ThreeC optionally substituted with alkyl_Three~ C₆Cycloa
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~ C₆Alkynyl
Sulfinyl, C_Two~ C₆Alkynylsulfonyl, C₁~
C_FourHaloalkylsulfenyl, C₁~ C_FourHaloalkyl
Sulfinyl, C₁~ C_FourHaloalkylsulfonyl, C_Two
~ C₆Haloalkenylsulfenyl, C_Two~ C₆Haloal
Kenylsulfinyl, C_Two~ C6 haloalkenylsulfoni
Le, C_Two~ C₆Haloalkynylsulfenyl, C_Two~ C₆C
Loalkynylsulfinyl, C_Two~ C₆Haloalkynyls
Ruphonyl, NO_Two, CN, -NU¹U^Two, Phenoxy, OH,
Naphthyl, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourA
Lucoxyalkyl, C_Two~ C_FourAlkylcarbonyl, C_Two
~ C_FiveAlkylcarbonyloxy, C_Two~ C_FiveHaloalk
Carbonyl, benzo optionally substituted with Z
Yl, phenyl optionally substituted with Z, substituted with Z
Pyridyl which may be optionally substituted with Z
Nil or -N = CT⁷T⁸Or adjacent
R¹Or R^TwoTogether with a 5-membered alkylene group
Ring, 6-membered ring, 7-membered ring or 8-membered ring (provided that R¹Is 2
When the number is more than one, they may be the same or different from each other. ), R^Two
Is H, C₁~ C_TenAlkyl, halogen or C₁~ C_Four
Substituted with phenyl optionally substituted with alkyl
C₁~ C_FourAlkyl, C_Two~ C₆Alkenyl, C_Two~ C₆A
Lucinyl, C₁~ C₆Haloalkyl, C₁~ C_ThreeWith alkyl
Optionally substituted C_Three~ C₆Cycloalkyl, nafti
Le, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourAlkoki
Sialkyl, C_Two~ C_FourAlkylcarbonyl, substituted with Z
Optionally substituted benzoyl, optionally substituted with Z
Phenyl, pyridyl optionally substituted with Z, substituted with Z
Optionally thienyl or -N = CT⁷T⁸Is
Or adjacent R¹Or R^TwoTogether with an alkylene group
5-, 6-, 7- or 8-membered ring formed
(Where R^TwoIf two or more are the same or different
May be. ), Y is H, C₁~ C_TenAlkyl, C_Two~
C₆Alkenyl, C_Two~ C₆Alkynyl, C₁~ C₆Haloa
Luquil, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy
Si, C_Two~ C ₆Alkynyloxy, C₁~ C_FourHaloalkoki
Si, C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Haloal
Quinyloxy, C₁~ C_FourMay be substituted with alkyl
Allyloxy, C₁~ C_FourAlkylsulfenyl, C₁
~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfo
Nil, C₁~ C_ThreeC optionally substituted with alkyl_Three~
C₆Cycloalkyl, CN, -NU¹U^Two, -C (= O) T¹,
C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FiveMonoalkylur
Minothiocarbonyl, C_Three~ C₉Dialkylaminothioca
Rubonil, C_Two~ C₆Alkylthiocarbonyl, morpholy
Pyrazolyl optionally substituted with nil, piperidyl and Z
I, imidazolyl optionally substituted with Z, substituted with Z
Pyrazolinyl which may be optionally substituted by Z
Pyridyl optionally substituted with phenyl or Z
Yes or R¹Or R^TwoTogether with an alkylene group
A 5-, 6-, 7- or 8-membered ring formed by
(However, when X is O, Y is alkyl or alkoxy.
Not. ), T¹But C₁~ C₂₀Alkyl, C_Two~ C₆Al
Kenil, C₁~ C₆Haloalkyl, C ₁~ C_FourAlkoxy-
C₁~ C_FourAlkyl, C_Three~ C₆Halocycloalkyl, halo
Gen or C₁~ C_FourOptionally substituted with alkyl
C substituted with phenyl₁~ C_FourAlkyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
Halogen or C₁~ C_FourEven if substituted with alkyl
Good phenyl substituted cycloalkyl, halogen also
Or C₁~ C_FourPhenyl optionally substituted with alkyl
Le and C₁~ C_FourCyclopropyl substituted with alkyl, ha
Logen or C₁~ C_FourEven if substituted with alkoxy
C substituted with good phenyl and halogen_Three~ C_FourCycloa
Alkyl optionally substituted with halogen_Two~ C_FourA
Lucenyl and C₁~ C_FourCyclopropyl substituted with alkyl
Group, halogen or C₁~ C_FourSubstituted with an alkyl group
Optionally substituted with phenyl_Two~ C_FourAlkene
Le, C₁~ C₁₂Alkoxy, C₁~ C_FourHaloalkoxy,
C_Two~ C_FiveAlkenyloxy, C₁~ C_ThreeSubstituted with alkyl
C that may be_Three~ C₆Cycloalkoxy, benzylo
Kissi, C_Two~ C_FiveAlkoxycarbonyl, -NU¹U^Two, Feni
Ruamino, phenyl optionally substituted with Z,
Optionally substituted phenoxy, even if substituted with Z
Good phenylthio, naphthyl optionally substituted by Z
Or a 5- or 6-membered ring optionally substituted with Z
Heterocyclic groups (however, these heterocyclic groups are thienyl,
, Oxazolyl, thiazolyl, pyrazolyl and pyridi
Selected from among ) Is the ethylene according to the above [1].
Derivatives.

[3] Q is Q-14, Q-15, Q-
16, Q-17, Q-18, Q-19, Q-20, Q-
21, Q-32, Q-33, Q-34, Q-35, Q-
36, Q-37, Q-44, Q-45, Q-46, Q-
47, Q-48, Q-49, Q-50, Q-51, Q-
52. The ethylene derivative according to the above [2], which is Q-53, Q-54, Q-79 or Q-80.

[4] Q is Q-18, Q-19, Q-
20, Q-21, Q-32, Q-33, Q-34, Q-
35, Q-36, Q-37, Q-44, Q-45, Q-
46, Q-47, Q-48, Q-49, Q-50, Q-
The ethylene derivative according to the above [3], which is 51, Q-52, Q-53, Q-54 or Q-80.

[5] Q is Q-18, Q-20, Q-
32, Q-33, Q-34, Q-36, Q-45, Q-
The ethylene derivative according to the above [4], which is 46, Q-47, Q-48, Q-51, Q-53 or Q-54.

[6] A is A-1, A-2, A-6,
A-9, A-10, A-11, A-12, A-13, A
-14, A-15, A-16, A-17, A-24, A
-25, A-26, A-27, A-34, A-36, A
The ethylene derivative according to the above [2], which is -38, A-44, A-50, A-51, A-52 or A-63.

[7] A is A-1, A-2, A-6,
A-9, A-10, A-11, A-12, A-13, A
-14, A-15, A-16, A-17, A-24, A
-25, A-26, A-27, A-34, A-36, A
The ethylene derivative according to the above [3], which is -38, A-44, A-50, A-51, A-52 or A-63.

[8] A is A-1, A-2, A-6,
A-9, A-10, A-11, A-12, A-13, A
-14, A-15, A-16, A-17, A-24, A
-25, A-26, A-27, A-34, A-36, A
The ethylene derivative according to the above [4], which is -38, A-44, A-50, A-51, A-52 or A-63.

[0033]

[9] A is A-1, A-2, A-6,
A-9, A-10, A-11, A-12, A-13, A
-14, A-15, A-16, A-17, A-24, A
-25, A-26, A-27, A-34, A-36, A
The ethylene derivative according to the above [5], which is -38, A-44, A-50, A-51, A-52 or A-63.

[0034] [10] X is an ethylene derivative according to [2], wherein a N-X ^1.

[0035] [11] X is an ethylene derivative described in [3] is an N-X ^1.

[0036] [12] X is an ethylene derivatives of the above-mentioned [4], wherein a N-X ^1.

[0037] [13] X is an ethylene derivatives of the above-mentioned [5], wherein a N-X ^1.

[0038] [14] X is an ethylene derivative according to [6], wherein a N-X ^1.

[0039] [15] X is an ethylene derivative according to [7], wherein a N-X ^1.

[0040] [16] X is an ethylene derivatives of the above-mentioned [8], wherein a N-X ^1.

[0041] [17] X is, the above is an N-X ¹

[9] The ethylene derivative according to the above.

[18] An agricultural chemical comprising at least one of the ethylene derivatives according to [1] to [17] as an active ingredient.

[19] An underwater biofouling inhibitor comprising, as an active ingredient, at least one of the ethylene derivatives according to [1] to [17].

[0044]

BEST MODE FOR CARRYING OUT THE INVENTION -C (CN) of compound (1) of the present invention
The C (OB)-moiety has two isomers of E-form and Z-form when B is other than a hydrogen atom, both of which are included in the present invention. When B is a hydrogen atom, tautomers exist, which are also included in the present invention.

Further, the substituent X of Q in the compound (1) of the present invention
Is NX ¹ , CH-X ¹ or C- (X ¹ ) ₂ , there are two isomers, E-form and Z-form, both of which are included in the present invention.

Next, Q, A, B, R, R ¹ , R ² , R ³ ,
R ⁴ , G, G ¹ , X, X ¹ , Y, Z, T ¹ , T ² , T ³ , T ⁴ ,
^{T 5, T 6, T 7} , T 8, U 1, U 2, m, n, illustrating a preferred range of p or q.

Preferred ranges of Q are the following groups.

That is, QI: Q-14, Q-15, Q-1
6, Q-17, Q-18, Q-19, Q-20, Q-2
1, Q-32, Q-33, Q-34, Q-35, Q-3
6, Q-37, Q-44, Q-45, Q-46, Q-4
7, Q-48, Q-49, Q-50, Q-51, Q-5
2, Q-53, Q-54, Q-79, Q-80. QII: Q-18, Q-19, Q-20, Q-21, Q-
32, Q-33, Q-34, Q-35, Q-36, Q-
37, Q-44, Q-45, Q-46, Q-47, Q-
48, Q-49, Q-50, Q-51, Q-52, Q-
53, Q-54, Q-80. QIII: Q-18, Q-20, Q-32, Q-33, Q
-34, Q-36, Q-45, Q-46, Q-47, Q
-48, Q-51, Q-53, Q-54.

Preferred ranges of A are the following groups.

That is, AI: A-1, A-2, A-3, A
-4, A-5, A-6, A-7, A-8, A-9, A-
10, A-11, A-12, A-13, A-14, A-
15, A-16, A-17, A-18, A-19, A-
20, A-21, A-22, A-23, A-24, A-
25, A-26, A-27, A-34, A-36, A-
38, A-39, A-40, A-41, A-42, A-
43, A-44, A-45, A-46, A-50, A-
51, A-52, A-55, A-56, A-63. AII: A-1, A-2, A-6, A-9, A-10, A
-11, A-12, A-13, A-14, A-15, A
-16, A-17, A-24, A-25, A-26, A
-27, A-34, A-36, A-38, A-44, A
-50, A-51, A-52, A-63. AIII: A-1, A-2, A-6, A-9, A-10,
A-11, A-12, A-13, A-16, A-17,
A-24, A-25, A-26, A-27, A-36,
A-44, A-50, A-51, A-52, A-63. AIV: A-1, A-10, A-13, A-16, A-2
4, A-26, A-27, A-50, A-51, A-5
2, A-63.

Preferred ranges of B are the following groups.

That is, BI: H, C1-C_FourAlkyl, C₁~
C_FourHaloalkyl, C_Two~ C_FourAlkoxyalkyl, CH_Three
OC_TwoH_FourOCH_Two, C₁~ C_FourAlkylsulfonyl, halo
Gen or C₁~ C_FourOptionally substituted with alkyl
Phenylsulfonyl, -SO _TwoCF_Three, C_Two~ C₈Dialki
Luminosulfonyl, C_Three~ C₉Dialkylaminothioca
Rubonil, C_Three~ C₉Alkoxycarbonylalkyl,-
C (= O) T¹, -P (= O) T^TwoT^Three, -P (= S) T^Two
T^Three, Alkali metal atom, alkaline earth metal atom or
NHT^FourT5T6.

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

BIII: H, C ₁ -C ₄ alkyl, C ₂ -C ₄
Alkoxyalkyl, CH ₃ OC ₂ H ₄ OCH ₂ , C ₁ -C ₄
^{Alkylsulfonyl, -C (= O) T 1} , alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ^6.

[0055] BIV: H, C1~C ₄ alkyl, C ₂ -C _{4 alkoxyalkyl, CH 3 OC 2 H 4 OCH} 2, -C (=
O) T ¹ , alkali metal atom, alkaline earth metal atom or NHT ⁴ T ⁵ T ⁶ .

Preferred ranges of R are the following groups.

[0057] That is, RI: halogen, C ₁ -C ₆ alkyl, halogen or C ₁ -C ₄ alkyl substituted with phenyl which is substituted C ₁ -C ₃ alkyl, C ₁
-C ₆ haloalkyl, C ₁ -C ₃ alkyl substituted optionally C ₃ even though -C ₆ cycloalkyl, 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 ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄
Alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl, alkynylsulfinyl of _{C 2 ~C 4, C 2 ~C} 4 alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄
Haloalkenylsulfonyl, NO ₂ , CN, -NU ¹ U ² , naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, phenyl optionally substituted with Z A pyridyl optionally substituted with Z, a thienyl optionally substituted with Z, or a 5-membered ring, a 6-membered ring, a 7-membered ring formed by an alkylene group together with adjacent R or R ² 8-member ring.

RII: halogen, C₁~ C₆Alkyl, halo
Gen or C₁~ C_FourOptionally substituted with alkyl
C substituted with phenyl₁~ C_ThreeAlkyl, C₁~ C₆Halo
Alkyl, C₁~ C_ThreeC optionally substituted with alkyl
_Three~ C₆Cycloalkyl, NO _Two, CN, -NU¹U^Two, Nahchi
Le, C_Two~ C_FourAlkoxycarbonyl, C_Two~ C_FourAlkoki
Sialkyl, C_Two~ C_FourAlkylcarbonyl, substituted with Z
Optionally substituted with phenyl or Z
Pyridyl.

RIII: halogen, C ₁ -C ₆ alkyl, C ₁
-C ₆ haloalkyl, C ₁ -C ₃ alkyl substituted optionally C ₃ even though -C _{6 ^{cycloalkyl, NO 2, CN, -NU 1}} U
_² ,, C ^{2 ~C} ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, pyridyl which may be substituted by phenyl which may be substituted, or Z in Z.

Preferred ranges of R ¹ are the following groups.

That is, R ¹ I: H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₃ alkyl substituted with halogen or phenyl which may be substituted with C ₁ -C ₄ alkyl,
₁ -C ₆ haloalkyl, C ₁ -C ₃ alkyl optionally substituted C ₃ -C ₆ cycloalkyl, 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 ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄
Alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl, alkynylsulfinyl of _{C 2 ~C 4, C 2 ~C} 4 alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl, C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄
Haloalkenylsulfonyl, NO ₂ , CN, -NU ¹ U ² , naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, phenyl optionally substituted with Z , A pyridyl optionally substituted with Z, a thienyl optionally substituted with Z, or a 5-, 6-, or 7-membered ring formed by an alkylene group together with adjacent R ¹ or R ² Or an 8-member ring.

R ¹ II: H, halogen, C ₁ -C ₆ alkyl,
Halogen or C ₁ -C ₄ alkyl C ₁ -C ₃ alkyl substituted by phenyl optionally substituted, C ₁ -C ₆
Haloalkyl, C ₁ -C ₃ alkyl substituted optionally C ₃ even though -C _{6 ^{cycloalkyl, NO 2, CN, -NU 1}} U 2, naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxy Alkyl, C ₂ -C ₄ alkylcarbonyl, phenyl optionally substituted with Z or pyridyl optionally substituted with Z.

R¹III: H, halogen, C_{1 ~}C₆Archi
Le, C₁~ C₆Haloalkyl, C₁~ C_ThreeSubstituted with alkyl
C that may be_Three~ C₆Cycloalkyl, NO_Two, C
N, -NU¹U ^Two, C_Two~ C_FourAlkoxycarbonyl, C_Two~ C_Four
Alkoxyalkyl, C_Two~ C_FourAlkylcarbonyl, Z
Optionally substituted with phenyl or substituted with Z
Pyridyl that may be.

Preferred ranges of R ² are the following groups.

That is, R ² I: H, C ₁ -C ₆ alkyl, C ₁ -C ₃ alkyl substituted with halogen or phenyl which may be substituted with C ₁ -C ₄ alkyl, C ₁ -C ₆ Haloalkyl, C ₁ -C ₃ alkyl optionally substituted with C ₃ -C ₃ alkyl
₃ -C ₆ cycloalkyl, naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, phenyl optionally substituted by Z, which may be substituted with Z 5-, 6-, 7- or 8-membered rings which are good pyridyls, thienyls optionally substituted by Z or which are formed by an alkylene group together with adjacent R, R ¹ or R ² .

R ² II: H, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl optionally substituted by C ₁ -C ₃ alkyl, C ₂ -C ₄ alkoxy Carbonyl optionally substituted with carbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl or Z.

R ² III: H, C ₁ -C ₆ alkyl, C ₁ -C ₆
Haloalkyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ ~
C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl.

Preferred ranges of R ³ are the following groups.

That is, R ³ I: H, C ₁ -C ₆ alkyl.

Preferred ranges of R ⁴ are the following groups.

That is, R ⁴ I: H, C ₁ -C ₆ alkyl, C ₁ -C ₃ alkyl substituted with halogen or phenyl which may be substituted with C ₁ -C ₄ alkyl, C ₁ -C ₆ Haloalkyl, C ₁ -C ₃ alkyl optionally substituted with C ₃ -C ₃ alkyl
₃ -C ₆ cycloalkyl, naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, phenyl optionally substituted by Z, which may be substituted with Z 5-, 6-, 7- or 8-membered rings which are good pyridyls, thienyls optionally substituted by Z or which are formed by an alkylene group together with adjacent R, R ¹ or R ² .

R ⁴ II: H, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl optionally substituted by C ₁ -C ₃ alkyl, C ₂ -C ₄ alkoxy Carbonyl optionally substituted with carbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl or Z.

R ⁴ III: H, C ₁ -C ₆ alkyl, C ₁ -C ₆
Haloalkyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ ~
C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl.

Preferred ranges of G are the following groups.

That is, GI: 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 ₂ -C ₄ alkenyl Le phenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkyl Nils Le phenyl,
C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁
-C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ halo alkenyl Le phenyl,
C ₂ -C ₄ halo alkenylsulfinyl, C ₂ -C ₄ haloalkenyl sulfonyl, C ₂ -C ₄ haloalkylene Nils Le phenyl, C ₂ -C ₄ halo alkynylsulfinyl, C ₂ -C ₄
Haloalkynylsulfonyl, NO ₂ , CN, -NU ¹ U ² , C ₂
-C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₄ haloalkylcarbonyl, C ₂ -C ₄ alkylcarbonyloxy,
C ₂ -C ₄ halo alkylcarbonyloxy, 5-membered ring formed by an alkylene group, or adjacent G or with G ¹ is phenyl optionally substituted by Z,
6-membered ring, 7-membered ring or 8-membered ring.

GII: 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
G is an alkoxycarbonyl or adjacent G
K is G¹Together with a 5-membered ring formed by an alkylene group,
6-membered, 7-membered or 8-membered ring.

GIII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₆ alkoxycarbonyl.

Preferred ranges of G ¹ are the following groups.

That is, G ¹ I: H, C ₁ -C ₆ alkyl, C ₁ -C ₆
C ₄ haloalkyl, C2~C ₄ alkoxycarbonyl, C ₂
-C ₄ alkoxyalkyl 5, formed by C ₂ -C ₄ alkylcarbonyl, an alkylene group or phenyl which may be substituted with Z, or with adjacent G
Member ring, 6 member ring, 7 member ring or 8 member ring.

G ¹ II: H, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄
Alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl.

Preferred ranges of X are the following groups.

That is, XI: NX ¹ or CH-X ¹ .

XII: NX ¹ .

Preferred ranges of X ¹ are the following groups.

That is, X ¹ I: C ₁ -C ₆ alkyl, C ₁ -C ₄
Haloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkynyloxy , C ₂ -C ₆ allyloxy, C ₁ -C ₄
Alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C optionally substituted with ₃ alkyl C ₃ -C ₆ cycloalkyl, N
^{_{O 2, CN, -NU 1 U}} 2, OH, C 2 ~C 7 alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₅ haloalkylcarbonyl, C ₂ ~
C ₅ alkylcarbonyloxy, C ₂ -C ₅ halo alkylcarbonyloxy, C ₃ -C ₇ dialkylaminocarbonyloxy, may benzoyl optionally substituted by Z, substituted by phenyl or Z optionally substituted by Z Phenoxy may be.

X ¹ II: C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₆ allyloxy, C ₁ -C ₄ alkylsulfur Phenyl, NO ₂ , CN, —NU ¹ U ² , OH, C ₂ -C ₇ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄
Alkylcarbonyl, optionally substituted by C ₂ -C ₅ alkylcarbonyloxy, or Z phenoxy.

Preferred ranges of Y are the following groups.

That is, YI: H, C₁~ C_TenAlkyl, C_Two~
C₆Alkenyl, C_Two~ C₆Alkynyl, C₁~ C₆Haloa
Luquil, C₁~ C₆Alkoxy, C₁~ C_FourHaloalkoki
Si, C _Two~ C₆Allyloxy, C₁~ C_FourAlkylsulfe
Nil, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourArchi
Rusulfonyl, C₁~ C_ThreeMay be substituted with alkyl
C_Three~ C₆Cycloalkyl, CN, -NU¹U^Two, -C (=
O) T¹, C_Two~ C_FourAlkoxyalkyl, morpholini
, Piperidyl, pyrazolyl optionally substituted with Z
I, imidazolyl optionally substituted with Z, substituted with Z
Pyrazolinyl which may be optionally substituted by Z
Phenyl, pyridyl optionally substituted with Z
Or R, R¹Or R^TwoTogether with an alkylene group
A 5-, 6-, 7- or 8-membered ring formed by

YII: C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₆ allyloxy,
C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₃ may be alkyl substituted C ₃ -C ₆ cycloalkyl, CN, -N
U ¹ U ² , —C (＝ O) T ¹ , C ₂ -C ₄ alkoxyalkyl, morpholinyl, piperidyl, pyrazolyl optionally substituted with Z, imidazolyl optionally substituted with Z, substituted with Z A 5-membered ring formed by an alkylene group together with R, R ¹ or R ² ,
Member ring, 7-member ring or 8-member ring.

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, NO 2, CN, CHO,} OH, -NU 1 U 2, phenyl,
A substituent arbitrarily selected from phenoxy and C ₂ -C ₅ alkoxycarbonyl (however, when the number of the substituents is two or more, they may be the same or different from each other); Is 1, 2, 3, 4 or 5.

ZII: halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ haloalkyl, C ₁ -C ₄ alkoxy, NO _2, CN
And C ₂ -C ₅ alkoxy optionally selected substituents from the carbonyl (provided that the substituents may be the case of two or more different in the same or another.) Comprising the number of the substituent One, two or three.

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.
To 5, preferably 0 to 4, and more preferably 0, 1, 2, or 3. When the ring substituted by Z is naphthyl, the number of Z is an integer of 0 to 7, and preferably 0. When the ring substituted by Z is a heterocyclic group, the number of Z differs depending on the heterocyclic ring, and the heterocyclic ring is 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,
In the case of 4-thiadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Z is 0.
Or 1. The heterocycle is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,2,3-
Triazolyl, 1,3,5-triazinyl or 1,
In the case of 2,4-triazinyl, the number of Z is an integer of 0 to 2, preferably 1 or 2. When the heterocycle is thienyl, 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, more preferably 1 or 2. is there. When the heterocyclic ring is pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Z is an integer of 0 to 4, preferably 0 to 2, more preferably 1 or 2.
It is.

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 optionally substituted by alkyl C ₃ -C ₆ cycloalkyl, halogen or C ₁ -C ₄ alkyl substituted with phenyl optionally substituted cycloalkyl, halogen or C ₁ -C ₄ alkyl group in it substituted with phenyl which is substituted C ₂ -C ₄ alkenyl, C ₁ ~
C ₁₀ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₁ -C optionally substituted with ₃ alkyl C ₃ -C ₆ cycloalkoxy, benzyloxy, C ₂
~ C ₅ alkoxycarbonyl, -NU ¹ U ² , phenyl optionally substituted with Z, phenoxy optionally substituted with Z, phenylthio optionally substituted with Z, naphthyl or substituted with Z (However, this heterocyclic group may be thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-
Oxadiazolyl, 1,3,4-thiadiazolyl, 1,
2,4-thiadiazolyl, 1,2,4-triazolyl,
1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl or 1,2,4-triazinyl Selected from inside. ).

T¹II: C₁~ C₁₈Alkyl, C_Two~ C₆Al
Kenil, C₁~ C_FourHaloalkyl, C _Two~ C_FourAlkoxya
Lucyl, halogen or C₁~ C_FourSubstituted with alkyl
Optionally substituted with phenyl₁~ C_FourAlkyl,
C₁~ C_ThreeC optionally substituted with alkyl_Three~ C₆Shiku
Loalkyl, halogen or C₁~ C_FourSubstitute with alkyl
Optionally substituted phenyl-substituted cycloalkyl
Le, halogen or C ₁~ C_FourSubstituted with an alkyl group
Optionally substituted phenyl substituted C_Two~ C_FourAlkenyl,
C₁~ C_TenAlkoxy, C₁~ C_FourHaloalkoxy, C_Two~
C_FiveAlkenyloxy, C_Three~ C₆Cycloalkoxy,
Ndyloxy, C_Two~ C_FiveAlkoxycarbonyl, substituted with Z
Optionally substituted phenyl, optionally substituted with Z
Substituted with phenoxy, phenylthio, naphthyl or Z
A heterocyclic group which may be
Nil, furyl, oxazolyl, thiazolyl, pyrazolyl
Or selected from pyridinyl. ).

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 ₂ -C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy, benzyloxy, C
₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted by Z, which may be substituted with Z phenoxy, phenylthio, naphthyl, optionally substituted optionally substituted with also pyrazolyl or Z in Z pyridinyl It is.

Preferred ranges of T ² are the following groups.

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

The preferred range of T ³ is the following group.

That is, T ³ I is phenyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ alkylsulfenyl.

The preferred range of T ⁴ is the following group.

That is, T ⁴ I: H, C ₁ -C ₄ alkyl, C ₃
-C ₆ or a cycloalkyl group 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, contain nitrogen or sulfur atom It forms a 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 a cycloalkyl group 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, contain nitrogen or sulfur atom It forms a 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 a cycloalkyl group 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, contain nitrogen or sulfur atom It forms a 5-, 6- or 7-membered ring group.

The preferred range of T ⁷ is the following group.

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. .

The preferred range of T ⁸ is the following group.

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.

[0112] Preferred U ¹ range is the following group.

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

Preferred ranges of U ² are the following groups.

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

The preferable range of 1 is 0, 1 or 2, and more preferably 1 or 2.

The preferable range of m is 1, 2 or 3, and more preferably 1 or 2. The preferred range of n is 0, 1, 2 or 3, and more preferably 1 or 2.

A preferred range of p is 1 or 2.

Each group in the above-mentioned preferred substituents can be arbitrarily combined, and each represents a preferred range of the compounds of the present invention.

Next, B, R, R¹, R^Two, R^Three, R^Four, G, G
¹, X, X¹, Y, Z, T¹, T^Two, T ^Three, T^Four, T^Five, T⁶,
T⁷, T⁸, U¹Or U^TwoHere is an example.

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

B, R, R ¹ , R ² , R ³ , R ⁴ , G, G ¹ ,
^{X 1, Y, Z, T} 1, T 2, T 3, T 4, T 5, T 6, T 7, T
⁸ , the alkyl group in the definition of U ¹ or U ² includes a linear or branched alkyl group such as methyl, ethyl, n
-Propyl, isopropyl, n-butyl, isobutyl,
tert-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1,2
-Methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1,2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3- Methylpentyl, 4-
Methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, -Ethyl butyl, 1,
1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-undecyl, n-dodecyl, n-
Tridecyl, n-tetradecyl, n-pentadecyl, n
-Hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl and the like, each being selected within the range of the specified number of carbon atoms.

R, R ¹ , R ² , R ⁴ , G ¹ , X ¹ , Y, T ¹ ,
The alkenyl group in the definition of T ⁴ , T ⁵ or T ⁶ includes ethenyl as a linear or branched alkenyl group,
1-propenyl, 2-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 specified carbon number range.

The alkynyl group in the definition of R, R ¹ , R ² , R ⁴ , G ¹ , X ¹ or Y is ethynyl, 1-propynyl, 2-alkynyl as a linear or branched alkynyl group.
Propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2
-Pentynyl, 3-pentynyl, 4-pentynyl, 1-
Methyl-2-butynyl, 1-methyl-3-butynyl, 2
-Methyl-3-butynyl, hexynyl, 1-methyl-3
-Pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3
-Methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,
2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-
Butynyl and the like, and each is selected from the specified carbon number range.

B, R, R ¹ , R ² , R ⁴ , G, G ¹ , X ¹ ,
Y, The haloalkyl group in the definition of Z, or T ^1, linear or branched fluoromethyl group as haloalkyl group, chloromethyl group, bromomethyl group, fluoroethyl group, chloroethyl group, bromoethyl group, fluoro -n- propyl , Chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoro Methyl group, trifluorochloroethyl group, hexafluoro-n-propyl group, chlorobutyl group, fluorobutyl group, chloro-n-pentyl group, fluoro-n-pentyl group, chloro-n-hexyl group, fluoro-n-hexyl Groups, etc., It is selected from the range specified s number of carbon.

R, R ¹ , R ² , R ⁴ , G ¹ , X ¹ , Y, T ¹ , T
^{As the} C ₃ -C ₆ cycloalkyl group optionally substituted with a C ₁ -C ₃ alkyl group in the definition of ⁴ , T ⁵ or T ⁶ , a cyclopropyl group, a 1-methylcyclopropyl group,
2,2,3,3-tetramethylcyclopropyl group, cyclobutyl group, 1-ethylcyclobutyl group, 1-n-butylcyclobutyl group, cyclopentyl group, 1-methylcyclopentyl group, cyclohexyl group, 1-methylcyclohexyl And a 4-methylcyclohexyl group.

B, R, R¹, R^Two, R^Four, G¹Or T¹Constant
Halogen or C in the sense of ₁~ C_FourWith an alkyl group
C substituted with an optionally substituted phenyl group₁~ C_Four
Examples of the alkyl group include a benzyl group and 2-chlorobenzyl
Group, 3-bromobenzyl group, 4-chlorobenzyl group, 4
-Methylbenzyl group, 4-tert-butylbenzyl
Group, 1-phenylethyl group, 1- (3-chlorophenyl)
L) ethyl group, 2-phenylethyl group, 1-methyl-1
-Phenylethyl group, 1- (4-chlorophenyl) -1
-Methylethyl group, 1- (3-chlorophenyl) -1-
Methylethyl group, 1-phenylpropyl group, 2-phenyl
Propyl group, 3-phenylpropyl group, 1-phenyl
Butyl group, 2-phenylbutyl group, 3-phenylbutyl
Group, 4-phenylbutyl group, 1-methyl-1-phenyl
Propyl group, 1-methyl-2-phenylpropyl group, 1
-Methyl-3-phenylpropyl group, 2-methyl-2-
Phenylpropyl group, 2- (4-chlorophenyl) -2
-Methyl-propyl group, 2-methyl-2- (3-methyl
A phenyl) propyl group.

The C ₃ -C ₆ cycloalkyl group substituted by a halogen atom or a phenyl group which may be substituted by a C ₁ -C ₄ alkyl group in the definition of T ¹ includes 1-phenylcyclopropyl, 1-phenyl (3-chlorophenyl) cyclopropyl group, 1- (4-chlorophenyl) cyclopropyl group, 1- (4-bromophenyl) cyclopropyl group, 1- (4-fluorophenyl) cyclopropyl group,
1- (4-ethylphenyl) cyclopropyl group, 1-
(4-propylphenyl) cyclopropyl group, 2-phenylcyclopropyl group, 1-phenylcyclobutyl group,
2-phenylcyclobutyl group, 1-phenylcyclopentyl group, 1- (4-chlorophenyl) cyclopentyl group, 2-phenylcyclopentyl group, 3-phenylcyclopentyl group, 1-phenylcyclohexyl group, 1-
(3-fluorophenyl) cyclohexyl group, 1- (4
-Chlorophenyl) cyclohexyl group, 1- (4-tert-butylphenyl) cyclohexyl group, 2-phenylcyclohexyl group, 3-phenylcyclohexyl group, 4-phenylcyclohexyl group and the like.

A phenyl group which may be substituted by a halogen atom or a C ₁ -C ₄ alkyl group in the definition of T ¹
₁ -C ₄ as cyclopropyl group substituted by an alkyl group, 2,2-dimethyl-1-phenyl-cyclopropyl group, 1- (4-chlorophenyl) -2,2-dimethyl-cyclopropyl, 2,2 Dimethyl-3-phenylcyclopropyl group, 3- (3-chlorophenyl) -2,2-
Dimethylcyclopropyl group, (4-chlorophenyl)-
2,2-dimethyl-3-phenylcyclopropyl group,
(4-bromophenyl) -2,2-dimethyl-3-phenylcyclopropyl group, 2,2-dimethyl-3- (4-
Methylphenyl) cyclopropyl group, (4-tert-butylphenyl) -2,2-dimethyl-3-phenylcyclopropyl group and the like.

In the definition of T ^1, a phenyl group which may be substituted by a halogen atom or a C ₁ -C ₄ alkoxy group and a C ₃ -C ₄ cycloalkyl group substituted by a halogen atom include 2,2-dichloro -1-phenylcyclopropyl group, 2,2-dichloro-1- (3-chlorophenyl) cyclopropyl group, 2,2-dichloro-1- (4-
A methoxyphenyl) cyclopropyl group, a 2,2-dichloro-1- (4-ethoxyphenyl) cyclopropyl group,
2,2-dichloro-1- (4-i-propyloxyphenyl) cyclopropyl group, 2,2-dichloro-1- (4
-T-butylphenyl) cyclopropyl group, 2,2-dichloro-1- (4-methoxyphenyl) -3-phenylcyclopropyl group, 1- (4-ethoxyphenyl)-
And a 2,2,3,3-tetrafluorobutyl group.

In the definition of T ^1, the C ₂ -C ₄ alkenyl group optionally substituted by a halogen atom and the cyclopropyl group substituted by a C ₁ -C ₄ alkyl group include 2,2-
Dimethyl-3- (2,2-dimethylethenyl) cyclopropyl group, 3- (2,2-dibromoethenyl) -2,2
-Dimethylcyclopropyl group, 3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropyl group, 3-
And a (2,2-chlorotrifluoroethenyl) -2,2-dimethylcyclopropyl group.

The C ₃ -C ₆ cycloalkoxy group which may be substituted with a C ₁ -C ₃ alkyl group in the definition of T ¹ includes a cyclopropoxy group, a cyclobutoxy group, a cyclopentoxy group, a cyclohexyloxy group, And a 1-methylcyclopropoxy group.

Examples of the C ₂ -C ₄ alkenyl group substituted by a halogen atom or a phenyl group which may be substituted by a C ₁ -C ₄ alkyl group in the definition of T ¹ include 1-phenylethenyl and 2- Phenylethenyl group, 2- (2-
Chlorophenyl) ethenyl group, 2- (3-chlorophenyl) ethenyl group, 2- (4-chlorophenyl) ethenyl group, 2- (4-methylphenyl) ethenyl group, 2-
(2,6-difluorophenyl) ethenyl group, 2-
(2,5-dimethylphenyl) ethenyl group, 1-methyl-2-phenylethenyl group, 2-phenyl-1-propenyl group, 2- (4-bromophenyl) -1-propenyl group, 2- (2 4,6-trimethylphenyl) -1-propenyl group.

As the alkoxy group in the definition of R, R ¹ , G, X ¹ , Y, Z, T ¹ , T ² or T ³ , methoxy, ethoxy, n -Propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert
-Butoxy group, n-pentyloxy group, 1-methylbutyloxy group, 2-methylbutyloxy group, 3-methylbutyloxy group, 1,1-dimethylpropoxy group, 1,2
-Dimethylpropoxy group, 2,2-dimethylpropoxy group, 1-ethylpropyloxy group, n-hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group, 3-methylpentyloxy group, 4-methyl Pentyloxy group, 1,1-dimethylbutyloxy group,
1,2-dimethylbutyloxy group, 1,3-dimethylbutyloxy group, 2,2-dimethylbutyloxy group, 2,
3-dimethylbutyloxy group, 3,3-dimethylbutyloxy group, 1-ethylbutyloxy group, 2-ethylbutyloxy group, 1,1,2-trimethylpropyloxy group, 1,2,2-trimethylpropyloxy Group, 1-ethyl-1-methylpropyloxy group and 1-ethyl-2
-Methylpropyloxy group, n-heptyloxy group, n
-Octyloxy group, n-nonyloxy group, n-decyloxy group and the like, and each is selected from the specified carbon number range.

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

In the definition of R, R ¹ , G, X ¹ , Y, Z or T ¹ , -NU ¹ U ² represents methylamino, ethylamino, n-propylamino, isopropylamino,
n-butylamino group, isobutylamino group, sec-butylamino group, tert-butylamino group, n-pentylamino group, 1-methylbutylamino group, 2-methylbutylamino group, 3-methylbutylamino group, 1 1,1-dimethylpropylamino group, 1,2-dimethylpropylamino group, 2,2-dimethylpropylamino group, 1-ethylpropylamino group, n-hexylamino group, 1-methylpentylamino group, 2-methylpentyl Amino group, 3
-Methylpentylamino group, 4-methylpentylamino group, 1,1-dimethylbutylamino group, 1,2-dimethylbutylamino group, 1,3-dimethylbutylamino group,
2,2-dimethylbutylamino group, 2,3-dimethylbutylamino group, 3,3-dimethylbutylamino group, 1-
Ethylbutylamino group, 2-ethylbutylamino group,
1,1,2-trimethylpropylamino group, 1,2,2
-Trimethylpropylamino group, 1-ethyl-1-methylpropylamino group and 1-ethyl-2-methylpropylamino group, dimethylamino group, diethylamino group,
-n-propylamino group, diisopropylamino group, di-
n-butylamino group, di-sec-butylamino group, diisobutylamino group, di-n-pentylamino group, di-
n-hexylamino group, methylethylamino group, methylpropylamino group, methylisopropylamino group, methylbutylamino group, methyl-sec-butylamino group,
Methyl isobutylamino group, methyl-tert-butylamino group, methylpentylamino group, methylhexylamino group, ethylpropylamino group, ethylisopropylamino group, ethylbutylamino group, ethyl-sec-butylamino group, ethylisobutylamino group , Ethylpentylamino group, ethylhexylamino group, phenylamino group, benzylamino group, N-methylacetamide group,
Examples include an N-ethylacetamide group, an N-phenylacetamide group, an N-acetylacetamide group, and the like.

The alkoxycarbonyl group in the definition of R, R ¹ , R ² , R ⁴ , G, G ¹ , X ¹ , Z and T ¹ includes methoxycarbonyl, ethoxycarbonyl, n
-Propoxycarbonyl group, iso-propoxycarbonyl group, n-butoxycarbonyl group, sec-butoxycarbonyl group, iso-butoxycarbonyl group, ter
and a t-butoxycarbonyl group.

The C ₁ -C ₄ haloalkoxy groups in the definitions of R, R ¹ , G, X ¹ , Y, Z and T ¹ each include C ₁
To C ₄ straight-chain or branched-chain haloalkoxy groups, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,
Bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy Group, pentafluoroethoxy group, trichloroethoxy group, trifluorochloroethoxy group, fluoropropoxy group, chloropropoxy group, bromopropoxy group, fluorobutoxy group, chlorobutoxy group, fluoro-iso-propoxy group and chloro-iso-propoxy group And so on.

The C ₁ -C ₄ alkylsulfenyl groups in the definitions of R, R ¹ , G, X ¹ , Y, Z, T ² and T ³ include methylthio, ethylthio, n-propylthio, iso- Propylthio group, n-butylthio group, is
o-butylthio group, sec-butylthio group, tert-
A butylthio group.

The C ₁ -C ₄ alkylsulfinyl groups in the definitions of R, R ¹ , G, X ¹ , Y and Z include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-
Examples thereof include a butylsulfinyl group, an iso-butylsulfinyl group, a sec-butylsulfinyl group, and a tert-butylsulfinyl group.

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

B, R, R ¹ , R ² , R ⁴ , G, G ¹ , X ¹ ,
As the C ₂ -C ₄ alkoxyalkyl group in the definition of Y or T ¹ , there may be mentioned a C ₁ -C ₃ alkoxy-methyl group, a C ₁ -C ₄ alkoxyalkyl group.
C ₂ alkoxy - ethyl group, a methoxyethoxymethyl group and methoxypropyl group.

As the C ₂ -C ₄ alkylcarbonyl group in the definition of R, R ¹ , R ² , R ⁴ , G, G ¹ , X ¹ , U ¹ or U ² , an acetyl group, a propionyl group, a butanoyl group,
an iso-butanoyl group.

The C ₂ -C ₅ haloalkylcarbonyl group in the definition of G or X ¹ includes a chloroacetyl group, a trifluoroacetyl group, a 3,3,3-trifluoropropionyl group, a pentafluoropropionyl group and the like.

C ₂ in the definition of R, R ¹ , G or X ¹
-C ₅ haloalkylcarbonyloxy group includes a chloroacetyloxy group, a trifluoroacetyloxy group,
3,3,3-trifluoropropionyloxy group, pentafluoropropionyloxy group and the like.

The C ₃ -C ₇ dialkylaminocarbonyloxy group in the definition of G or X ¹ includes a dimethylaminocarbonyloxy group, a diethylaminocarbonyloxy group, a di-i-propylaminocarbonyloxy group and the like.

The naphthyl group in the definition of R, R ¹ , R ² , R ⁴ , G ¹ and T ¹ includes a 1-naphthyl group and a 2-naphthyl group.

The pyridyl group which may be substituted with Z in the definition of R, R ¹ , R ² , R ⁴ , G ¹ , X ¹ , Y or T ¹ is 2-pyridyl which may be substituted with Z. Pyridyl group, 3-pyridyl group optionally substituted by Z or Z
A 4-pyridyl group optionally substituted with Z, preferably a 2-pyridyl group optionally substituted with Z or a 3-pyridyl group optionally substituted with Z, and more preferably Z It is a 2-pyridyl group which may be substituted.

The thienyl group which may be substituted with Z in the definition of R, R ¹ , R ² , R ⁴ , G ¹ or T ¹ includes a 2-thienyl group which may be substituted with Z and a thienyl group which may be substituted with Z. Examples thereof include an optionally substituted 3-thienyl group.

-N = CT ⁷ T ⁸ in the definition of R, R ¹ , R ² , R ⁴ , G and G ¹ represents an alkylideneamino group, a benzylideneamino group, an arylideneamino group or a cycloalkylideneamino group, Examples include a methylideneamino group, an ethylideneamino group, a propylideneamino group, an isopropylideneamino group, a 4-methyl-2-pentylideneamino group, a cyclopentylideneamino group, and a cyclohexylideneamino group.

Examples of the C ₁ -C ₄ alkylaminosulfonyl group in the definition of B include a methylaminosulfonyl group, an ethylaminosulfonyl group, an n-propylaminosulfonyl group, an isopropylaminosulfonyl group and an n-butylaminosulfonyl group. Can be

The C ₂ -C ₈ dialkylaminosulfonyl groups in the definition of B include dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, diisopropylaminosulfonyl and di-n-butylaminosulfonyl groups And so on.

The C ₂ -C ₅ alkylaminothiocarbonyl group in the definition of B includes methylaminothiocarbonyl group, ethylaminothiocarbonyl group, n-propylaminothiocarbonyl group, isopropylaminothiocarbonyl group and n-butylamino And a thiocarbonyl group.

As the C ₃ -C ₉ dialkylaminothiocarbonyl group in the definition of B, dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-
A propylaminothiocarbonyl group, a diisopropylaminothiocarbonyl group and a di-n-butylaminothiocarbonyl group.

A halogen atom or C in the definition of B
Examples of the C ₁ -C ₄ alkyl group substituted with a benzoyl group which may be substituted with a ₁ -C ₄ alkyl group include a phenacyl group,
2-fluorophenacyl group, 3-chlorophenacyl group,
4-bromophenacyl group, 2-methylphenacyl group, 3
-Ethylphenacyl group, 4-i-propylphenacyl group, 4-t-butylphenacyl group and the like.

The halogen atom or C in the definition of B
₁ The -C ₄ alkyl optionally phenylsulfonyl group optionally substituted with a group, 2-fluorophenyl sulfonyl group, 4-fluorophenyl sulfonyl group, 2-chlorophenyl sulfonyl group, 4-chlorophenyl sulfonyl group,
4-bromophenylsulfonyl group, 2,5-dichlorophenylsulfonyl group, pentafluorophenylsulfonyl group, 4-methylphenylsulfonyl group, 2-methylphenylsulfonyl group, 4-t-butylphenylsulfonyl group,
Examples thereof include a 2,5-dimethylphenylsulfonyl group, a 2,4-dimethylphenylsulfonyl group, a 2,4,6-trimethylphenylsulfonyl group, and a 2,4,6-tri-i-propylphenylsulfonyl group.

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

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

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

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

The ammonium group represented by NHT ⁴ T ⁵ T ⁶ in the definition of B includes an ammonium group, a monomethyl ammonium group, a dimethyl ammonium group, a trimethyl ammonium group, a diethyl ammonium group, a triethyl ammonium group, a diisopropyl ammonium group, a diisopropyl ammonium group. Ammonium group, hexylmethylammonium group, cyclopropylmethylammonium group,
Cyclohexylmethylammonium group, allylmethylammonium group, benzylmethylammonium group or 4
A heterocycle which is a methylcyclohexylethylammonium group or which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which two of T ⁴ , T ⁵ and T ⁶ are respectively bonded Examples include a 5-, 6-, 7- or 8-membered ammonium group of the formula.

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

The haloalkylsulfenyl group in the definition of R, R ¹ , G or Z includes a C ₁ -C ₄ linear or branched haloalkylthio group such as fluoromethylthio, chlorodifluoromethylthio and bromodifluoro. Methylthio group, trifluoromethylthio group, trichloromethylthio group, 2,2,2, -trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, fluoroethylthio group, pentafluoroethylthio group and And fluoro-iso-propylthio groups.

The haloalkylsulfinyl group in the definition of R, R ¹ , G or Z includes a C ₁ -C ₄ linear or branched haloalkylsulfinyl group such as a fluoromethylsulfinyl group, a chlorodifluoromethylsulfinyl group and a bromodifluoromethylsulfinyl group. Difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2, -trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pentafluoro Examples include an ethylsulfinyl group and a fluoro-iso-propylsulfinyl group.

The haloalkylsulfonyl group in the definition of R, R ¹ , G or Z includes a C ₁ -C ₄ linear or branched haloalkylsulfonyl group such as a fluoromethylsulfonyl group, a chlorodifluoromethylsulfonyl group, and a bromodifluoro group. Methylsulfonyl group, trifluoromethylsulfonyl group, trichloromethylsulfonyl group, 2,2,2, -trifluoroethylsulfonyl group, 1,1,2,2
-A tetrafluoroethylsulfonyl group, a fluoroethylsulfonyl group, a pentafluoroethylsulfonyl group and a fluoro-iso-propylsulfonyl group.

The haloalkenyl group in the definition of R or R ¹ includes 2-chloroethenyl, 2-bromoethenyl, 2,2-dichloroethenyl and the like as a C ₂ -C ₄ linear or branched haloalkenyl group. Is raised.

In the definition of R, R ¹ , G, X ¹ , Y or T ¹ , the alkenyloxy group may be a C ₂ -C ₄ linear or branched alkenyloxy group such as an allyloxy group or a 2-propenyloxy group. , 2-butenyloxy group, 2-methyl-2-propenyloxy group and the like.

In the definition of R, R ¹ , G, X ¹ or Y, the haloalkenyloxy group is a C ₂ -C ₄ straight-chain or branched haloalkenyloxy group, which is 3-chloro-2-
Propenyloxy group, 3,3-dichloro-2-propenyloxy group, 4-chloro-2-butenyloxy group, 4,4-dichloro-3-
Butenyloxy group and 4,4-difluoro-3-butenyloxy group.

The alkenylsulfenyl group in the definition of R, R ¹ , G or Z includes allylsulfenyl, 2-propenylsulfenyl and C ₂ -C ₄ linear or branched alkenylsulfenyl. Examples thereof include a 2-butenylsphenyl group and a 2-methyl-2-propenylsulfenyl group.

The alkenylsulfinyl group in the definition of R, R ¹ , G or Z includes allylsulfinyl, 2-propenylsulfinyl, 2-butenyl as a C ₂ -C ₄ linear or branched alkenylsulfinyl group. Examples include a sphinyl group and a 2-methyl-2-propenylsulfinyl group.

The alkenylsulfonyl group in the definition of R, R ¹ , G or Z includes allylsulfonyl, 2-propenylsulfonyl, and 2-butenylsulfonyl as C ₂ -C ₄ linear or branched alkenylsulfonyl. And 2-methyl-2-propenylsulfonyl group.

The haloalkenylsulfenyl group in the definition of R, R ¹ or G includes 3-chloro as a C ₂ -C ₄ straight-chain or branched haloalkenylsulfenyl group.
2-propenylsulfenyl group, 4-chloro-2-butenylsulfenyl group, 3,3-dichloro-2-propenylsulfenyl group, 4,4-dichloro-3-butenylsulfenyl group, 4,4 -
And a difluoro-3-butenylsulfenyl group.

The haloalkenylsulfinyl group in the definition of R, R ¹ or G includes 3-chloro as a C ₂ -C ₄ linear or branched haloalkenylsulfinyl group.
-2-propenylsulfinyl group, 3,3-dichloro-2-propenylsulfinyl group, 4-chloro-2-butenylsulfinyl group, 4,4-dichloro-3-butenylsulfinyl group, 4,4-
And a difluoro-3-butenylsulfinyl group.

In the definition of R, R ¹ or G, the haloalkenylsulfonyl group may be a C ₂ -C ₄ linear or branched haloalkenylsulfonyl group,
Propenylsulfonyl group, 3,3-dichloro-2-propenylsulfonyl group, 4-chloro-2-butenylsulfonyl group, 4,4
-Dichloro-3-butenylsulfonyl group, 4,4-difluoro-3
-Butenylsulfonyl group and the like.

The C ₂ -C ₄ haloalkynyl group in the definition of R or R ¹ includes chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl, 3-bromo-1-butynyl And the like.

As the alkynyloxy group in the definition of R, R ¹ , G, X ¹ or Y, a 2-propynyloxy group,
Examples thereof include a 2-butynyloxy group and a 1-methyl-2-propynyloxy group.

The haloalkynyloxy group in the definition of R, R ¹ , G, X ¹ or Y includes 3-chloro-2-propynyloxy group, 3-bromo-2-propynyloxy group, 3-iodo-2- And a propynyloxy group.

C ₂ -C ₆ in the definition of R, R ¹ or G
Alkynylsulfenyl groups include 2-propynylsulfenyl group, 2-butynylsulfenyl group, 1-methyl-2-
And a propynylsulfenyl group.

C ₂ -C ₆ in the definition of R, R ¹ or G
Examples of the alkynylsulfinyl group include a 2-propynylsulfinyl group, a 2-butynylsulfinyl group, and 1-methyl-2-
And a propynylsulfinyl group.

C ₂ -C ₆ in the definition of R, R ¹ or G
Examples of the alkynylsulfonyl group include a 2-propynylsulfonyl group, a 2-butynylsulfonyl group, a 1-methyl-2-propynylsulfonyl group, and the like.

C ₂ -C ₆ in the definition of R, R ¹ or G
As the haloalkynylsulfenyl group, 3-chloro-2
-Propynylsulfenyl group, 3-bromo-2-propynylsulfenyl group, 3-iodo-2-propynylsulfenyl group and the like.

C ₂ -C ₆ in the definition of R, R ¹ or G
Haloalkynylsulfinyl groups include 3-chloro-2
-Propynylsulfinyl, 3-bromo-2-propynylsulfinyl, 3-iodo-2-propynylsulfinyl and the like.

C ₂ -C ₆ in the definition of R, R ¹ or G
Examples of the haloalkynylsulfonyl group include a 3-chloro-2-propynylsulfonyl group, a 3-bromo-2-propynylsulfonyl group, and a 3-iodo-2-propynylsulfonyl group.

Examples of the alkylcarbonyloxy group in the definition of R, R ¹ , G or X ¹ include an acetoxy group, a propanoyloxy group, a butanoyloxy group and an isopropylcarbonyloxy group.

The benzoyl group optionally substituted with Z in the definition of R, R ¹ , R ² , R ⁴ , G ¹ or X ¹ includes a benzoyl group, a 2-chlorobenzoyl group, a 3-chlorobenzoyl group, Examples thereof include a 4-chlorobenzoyl group, a 4-bromobenzoyl group, a 4-fluorobenzoyl group, a 3-methylbenzoyl group, a 4-methylbenzoyl group, a 4-tert-butylbenzoyl group, and a 3,4-dichlorobenzoyl group.

The allyloxy group optionally substituted by C ₁ -C ₄ alkyl in the definition of X ¹ or Y includes:
Allyloxy, 1-methylallyloxy, 2-methylallyloxy, 3-methylallyloxy, 1-ethylallyloxy, 2-ethylallyloxy, 3-
Ethyl allyloxy group, 1-propyl allyloxy group,
2-propylallyloxy group, 3-propylallyloxy group, 1-isopropylallyloxy group, 2-isopropylallyloxy group, 3-isopropylallyloxy group, 1-butylallyloxy group, 2-butylallyloxy group, 3 -Butyl allyloxy group and the like.

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

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

[0189] Nikameiga, Kobunomeiga, Futaobikoyaga, Ichimonjiseri, Konaga, Yotoga, Monshiro butterfly, Kabulayaga, Hasunyoto, Shiroichimonjioto, Chanokokakumonmonamaki, Chahamaki, Momomosinui, Nishihimemeshinkui, and Rabbit's Tobacco , European corn borer, fall army worm, codling moth, lepidopteran pests such as white-winged starling, black leafhopper, brown planthopper, peach peach aphid, cotton aphid, onsic whitefly, tobacco whitefly, pear white lice, tsutsujigumbai, shirakawagashi beetle Hemiptera pests such as stink bugs, stink bugs and bed bugs, Nijuya Shitentou, cupreous chafer,
Rice water weevil, Alimodoki weevil, turtle beetle,
Lepidoptera, Colorado potato beetle, Scotch beetle, Pine beetle, Pine beetle, Corn rootworm, Scotch elephant, Granary weevil, Scotch flies, etc.
Diptera pests such as sand flies, sheep flies, cynoid flies, bullflies, sheep flies, tsetse flies, mosquitoes, aedes aegypti, anopheles, etc. Pterodactyl pests such as Thrips palmi, black cockroaches, black cockroaches, German cockroaches such as German cockroaches, Orthoptera pests such as Tonosama grasshopper, Kobananeago, Saba-kuttaribatta, termite pests such as house termites, Japanese termites, and Japanese termites, Isopteran pests such as cat flea, human flea, and cepopterine flea, chicken lice,
Louse pests such as bovine lice, louse pests such as bovine lice, porcine lice, bovine lice, cephalic lice, citrus spider mites, apple spider mites, spider mites,
Spider mites, such as Kanzawa spider mite, red mite, red rust mite, red rust mite, tulip rust mite, red mite, swelling mite such as scrophular mite, cyclamen mite, red mite such as red mite, robin mite, and bee mite, such as bee mites. , Ox tick, Dermatophagoid mites such as Haemaphysalis longicornis;
Sweet potato nematode, northern root-knot nematode,
Northern nematode, walnut nematode,
Nematodes such as potato cyst nematodes and pine wood nematodes, mollusks such as black mussels, slugs, mussels and mussels, and crustaceans such as okadan bugs.

Further, the compound of the present invention is effective in preventing the adhesion of living organisms at a very low concentration. Examples of such aquatic organisms include shellfish and algae such as mussels, barnacles, oysters, hydramushi, hydra, serpula, sea squirts, bryozoans, fussbugs, snails, aosa, aonori and shiomidoro.

That is, the compounds of the present invention can effectively control pests and plant diseases of Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites and Lice, at low concentrations. it can. Furthermore, the compound of the present invention can control the adhesion of various aquatic organisms to seawater structures in seawater and freshwater. 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

[0194]

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[Q, A, B and Y in (Scheme 1)
Represents the same meaning as above, L is a good leaving group such as chlorine
Child, bromine atom, iodine atom, C₁~ C_FourAlkoxy group,
Enoxy group, C₁~ C_FourAlkylsulfonyloxy group,
Benzenesulfonyloxy group, toluenesulfonyloxy
Group, phenoxy group, 1-pyrazolyl group or 1-imidazoly
L ′ is a halogen atom, and alkyl is
Alkyl group, preferably C₁~ C _FourIt is an alkyl group. The method A in (Scheme 1) is represented by the general formula (2)
Acetonitrile derivative and acid chloride represented by general formula (3)
Chlorides, esters or amides or general formula
By reacting the acid anhydride represented by (4)
A method for synthesizing the light compound (1 ′) will be described. Further invention
Compound (1 ′) is an alkylhalai compound represented by the general formula (7)
, Alkylsulfonates, trimethylsilylhala
Ids, sulfonyl chlorides, sulfamoyl chloride
Rides, thiocarbamoyl chlorides, acid chlorides
Of the present invention by reacting
It can be converted to compound (1). At this time, the compound of the present invention
The compound of the present invention depending on the type of B in (1)
(1 ′) has dihydropyran, isocyanates or
Synthesized by reacting oisocyanates. In addition, by law A
(1) can also be synthesized without isolating (1 ′).

When Q is bonded to an acrylonitrile moiety by a nitrogen atom, it can also be synthesized by Method B. Method B is
A method for synthesizing the compound (1 ′) or (1) of the present invention by reacting the heterocyclic ring represented by the general formula (5) with the halogenocyanoketone derivative represented by the general formula (6) or (6 ′) Is shown.

When A is bonded to the acrylonitrile moiety by a nitrogen atom, it can be synthesized also by the method C. Method C refers to a method of synthesizing the compound of the present invention from a cyanoacetic acid derivative represented by the general formula (8) and a heterocyclic compound represented by the general formula (9). In some cases, the compound represented by the general formula (8) can be synthesized by reacting the acetonitrile derivative represented by the general formula (2) shown by the method A with a carbonate in the presence of a base.

In some cases, it can be synthesized by the D method. The method D is synthesized from the aromatic ring carbonyl compound represented by the general formula (10) synthesized by the method A, the method B or the method C. X ¹ -NH ₂ when X is NX ¹
Can be synthesized by reacting X is CH-X ¹ or C-
In the case of (X ¹ ) ₂ , condensation reaction with active methylene, Wit
Tig reaction, Wittig-Horner reaction, Pet
It can be synthesized by an Erson reaction or the like.

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

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

The compound of the present invention can be obtained from the reaction solution by a conventional method. However, if it becomes 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 (-).

The compound (2) in (Scheme 1) can be synthesized according to the method described in International Patent Application Publication (WO97 / 40009).

Examples of the compounds included in the present invention are described below. The abbreviations in the table have the following meanings.

Me: methyl group, Et: ethyl group, Pr:
Propyl group, Bu: butyl group, Pen: pentyl group, He
x: hexyl group, Hep: heptyl group, Oct: octyl group, Non: nonyl group, Dec: decyl group, Ph: phenyl group, n: normal, i: iso, sec: secondary, t: tertiary, c: cyclo , Pyridyl: pyridyl group, Piperidyl: piperidyl group, Pyrazolyl: pyrazolyl group, Morpholinyl: morpholinyl group, Imidazolyl:
Imidazolyl group, Pyrazolinyl: pyrazolinyl group

[0206]

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[0207]

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Table 1 shows the compound groups AA1 to ZZ1.

Table 1

[0210]

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[0211]

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[0212]

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[0213]

[Table 1] ――――――――――――――――――――――――――― Compound group BR ¹ R ² ――――――――――― ―――――――――――――――――― AA1 HHH BB1 HMe H CC1 C (O) tBu HH DD1 C (O) tBu Me H EE1 C (O) tBu Cl H FF1 C ( O) tBu H Me GG1 C (O) Me HH HH1 C (O) Ph HH II1 C (O) CF ₃ HH JJ1 C (O) (3-Pyridyl) HH KK1 C (O) (2,6-Me ₂ -Ph) HH LL1 C (O) NMe ₂ HH MM1 C (O) NHPh HH NN1 Me HH OO1 CH ₂ OCH ₃ HH PP1 CH ₂ OCH ₂ CH ₃ HH QQ1 CH ₂ O (CH ₂ ) ₂ OCH ₃ HH RR1 CH ₂ SCH ₃ HH SS1 CH ₂ Ph HH TT1 C (O) OMe HH UU1 C (O) OEt HH VV1 P (O) (OEt) ₂ HH WW1 SO ₂ Me HH XX1 SO ₂ Ph HH YY1 SO ₂ NMe ₂ HH ZZ1 SO ₂ CF ₃ HH ―――――――――――――――――――――――――――――

Table 2 shows examples of combinations of the substituents A, X and Y in each of the compound groups AA1 to ZZ1.

[0215]

[Table 2] Table 2 ―――――――――――――――――――――――――― AXY ―――――――――――――――― ―――――――――― A1 NOMe H A1 NOMe Me A1 NOMe Et A1 NOMe CO ₂ Me A1 NOMe CO ₂ Et A1 NOMe CN A1 NOMe OMe A1 NOMe NH ₂ A1 NOMe NHMe A1 NOMe NMe ₂ A1 NOEt Me A2 nOMe H A2 nOMe Me A2 nOMe Et A2 nOMe CO 2 Me A2 nOMe CO 2 Et A2 nOMe CN A2 nOMe OMe A2 nOMe NH 2 A2 nOMe NHMe A2 nOMe NMe 2 A2 NOEt Me A2 NOCH 2 CH = CH 2 Me A2 NOCH 2 CH = CH ₂ Et A2 NOCH ₂ CH = CH ₂ CO ₂ Me A2 NOCH ₂ CH = CH ₂ CO ₂ Et A2 CHCN Me A2 C (CN) ₂ Me A2 CHOMe Me A2 NPh Me A3 NOMe H A3 NOMe Me A3 NOMe Et A3 _{nOMe CO 2 Me A3 nOMe CO 2} Et A3 nOMe CN A3 nOMe OMe A3 nOMe NH 2 A3 nOMe NHMe A3 nOMe NEt 2 A3 NOEt Me A3 NOEt CO 2 Me A3 NOiPr Me A3 NOCH 2 CH = CH 2 Me A3 NOCH 2 CH = CH ₂ Et A3 NOCH ₂ CH = CH ₂ CO ₂ Me A3 NOCH ₂ CH = CH ₂ CO ₂ nBu A3 CHCN Me A3 C (CN) ₂ Me A3 C (CN) CO ₂ Me Me A3 NPh Me A4 NOMe Me A4 NOMe Et A4 NOMe nHex A4 NOMe CO ₂ Me A4 NOMe CO ₂ Et A4 NOMe CN A4 NO _{Me OMe A4 NOMe NH 2 A4 NOMe} NHMe A4 NOMe NEt 2 A4 NOnHex Me A4 NOCH 2 CH = CH 2 Me A4 NOCH 2 CH = CH 2 Et A4 NOCH 2 CH = CH 2 CO 2 Me A4 NOCH 2 CH = CH 2 SMe A4 CHCN Me A4 C (CN) ₂ Me A4 C (CN) CO ₂ Me Me A4 NPh Me A5 NOMe Me A5 NSMe Et A5 NCN COMe A5 NOMe CO ₂ Me A6 CHCO ₂ Me CH = CH ₂ A6 NOCH = CH ₂ CF ₃ A6 NNO ₂ CH ₂ OMe A6 NNMe ₂ C (S) NHMe A7 NCH = CH ₂ OCH = CH ₂ A7 CHC≡CH OCF ₃ A7 NOCF ₃ OCH ₂ CH = CH ₂ A7 N- (1-Piperidyl) cHex A8 NOMe Me A8 NOC≡CH 1-Pyrazolyl A8 NCOPh C≡CH A8 NOPh CO ₂ Me A9 NOMe Me A9 NCF ₃ OC≡CH A9 NOCONMe ₂ OCF = CF ₂ A9 NOEt CO ₂ Me A10 NOMe H A10 NOMe Me A10 NOH Me A10 NOH Et A10 nOMe Et A10 nOMe iPr A10 nOMe nHex A10 nOMe CO 2 Me A10 nOMe COMe A10 nOMe CO 2 Et A10 nOMe CONHMe A10 nOMe CONMe 2 A10 nOMe CN A10 nOMe OMe A10 nOMe OEt A10 nOMe SMe A10 nOMe NH 2 A10 nOMe NHMe A10 NOMe NMe ₂ A10 NOMe NEt ₂ A10 NOMe CF ₃ A10 NOEt Me A10 NOEt Et A10 NOEt CO ₂ Me A10 NOnPr Me A10 NOnBu Me A10 NOnOct C (S) Me A10 NOiPr Me A10 NOCH ₂ CH = CH ₂ Me A10 NOCH ₂ CH = CH ₂ Et A10 NOCH ₂ CH = CH ₂ C O ₂ Me A10 NOCH ₂ CH = CH ₂ CO ₂ Et A10 CHCN Me A10 C (CN) ₂ Me A10 C (CN) CO ₂ Me Me A10 CHOMe Me A10 CHNO ₂ Me A10 NPh Me A10 N- (2-Pyridyl) Me A10 NOPh Me A10 NOC (O) Me Me A10 NOC (O) tBu Me A10 NOC (O) CF ₃ Me A10 NSMe Et A10 NCN Me A10 NOCF = CF ₂ Ph A10 NOC≡CF cPr A10 NNO ₂ Me A10 NNO ₂ S (O) Me A10 NNMe ₂ Me A10 NNMe ₂ CO ₂ Me A10 NNMe ₂ SO ₂ Me A10 NS (O) Me C (S) NMe ₂ A10 NSO ₂ Me OC≡CF A10 NcHex 3-Pyridyl A10 NCH ₂ OMe 1 -Piperidyl A10 NCOMe 1-Imidazolyl A10 NCOCF ₃ 1-Pyrazolinyl A10 NCO ₂ Me 1-Morpholinyl A10 N- (1-Morpholinyl) Me A10 N- (1-Morpholinyl) CO ₂ Me A10 O Ph A10 O 3-Pyridyl A10 O 1-Piperidyl A10 O 1-Imidazolyl A10 O 1-Pyrazolinyl A10 O 1-Morpholinyl A10 S Ph A10 S 3-Pyridyl A10 S 1-Piperidyl A10 S 1-Imidazolyl A10 S 1-Pyrazolinyl A10 S 1-Morpholinyl A11 NOMe H A11 NOMe Me A11 NOMe Et A11 NOMe CO ₂ Me A11 NOMe CO ₂ Et A11 NOMe CN A11 NOMe OMe A11 NOMe NH ₂ A11 NOMe NHMe A11 NOMe NEt ₂ A11 NOEt Me A11 NOEt CO ₂ Me A11 NOiPr Me A11 NOCH ₂ CH = CH ₂ Me A11 NOCH ₂ CH = CH ₂ Et A11 NOCH ₂ CH = CH ₂ CO ₂ Me A11 NOCH ₂ CH = CH ₂ CO ₂ nBu A11 CHCN Me A11 C (CN) ₂ Me A11 C (CN) CO ₂ Me Me A11 NPh Me A12 NOMe H A12 NOMe Me A12 NOMe Et A12 NOMe CO ₂ Me A12 NOMe CO ₂ Et A12 NOMe CN A12 NOMe OMe A12 NOMe NH ₂ A12 NOMe NHMe A12 NOMe NEt ₂ A12 NOEt Me A12 NOEt CO ₂ Me A12 NOiPr Me A12 NOCH ₂ CH = CH ₂ Me A12 NOCH ₂ CH = CH ₂ Et A12 NOCH ₂ CH = CH ₂ CO ₂ Me A12 NOCH ₂ CH = CH ₂ CO ₂ nBu A12 CHCN Me A12 C (CN) ₂ Me A12 C (CN) CO ₂ Me Me A12 NPh Me A13 NOMe Me A13 NOEt Et A13 NOCH ₂ CH = CH ₂ Me A13 NOMe CO ₂ Me A14 NOMe Me A14 NOEt Me A14 NOCH ₂ CH = CH ₂ Me A14 NOMe CO ₂ Me A15 NOMe Me A15 NOEt Me A15 NOCH ₂ CH = CH ₂ iPr A15 NOMe CO ₂ Me A16 NOMe Me A16 NOEt Me A16 NOCH ₂ CH = CH ₂ NEt ₂ A16 NOMe CONHMe A17 NOMe Me A17 NOEt Me A17 NOCH ₂ CH = CH ₂ NEt ₂ A17 NOPh CONHMe A18 NOMe Me A18 NOEt Me A18 NOCH ₂ CH = CH ₂ NEt ₂ A18 NOC (O) tBu OnBu A19 NOMe Me A19 NOEt Me A19 NOCH ₂ CH = CH ₂ NnPr ₂ A19 NOMe OiPr A20 NOMe Me A20 NOEt Me A20 NOCH ₂ CH = CH ₂ COnBu A20 NSnBu OtBu A21 NOMe Me A21 NOEt Me A21 NOCH ₂ CH = CH ₂ CON HEt A21 NOtBu Me A22 NOMe Me A22 NOEt Me A22 NOCH ₂ CH = CH ₂ Me A22 NOMe CO ₂ Me A23 NOMe Me A23 NOEt Me A23 NOCH ₂ CH = CH ₂ Me A23 NOMe CO ₂ Me A24 NOMe H A24 NOMe Me A24 NOMe Et A24 NOMe CO ₂ Me A24 NOMe CO ₂ Et A24 NOMe CN A24 NOMe OMe A24 NOMe NH ₂ A24 NOMe NHMe A24 NOMe NEt ₂ A24 NOEt Me A24 NOEt CO ₂ Me A24 NOiPr Me A24 NOCH ₂ CH = CH ₂ Me A24 NOCH ₂ CH = CH ₂ Et A24 NOCH ₂ CH = CH ₂ CO ₂ Me A24 NOCH ₂ CH = CH ₂ CO ₂ nBu A24 CHCN Me A24 C (CN) ₂ Me A24 C (CN) CO ₂ Me Me A24 NPh Me A25 NOMe H A25 NOMe Me A25 NOMe Et A25 NOMe CO ₂ Me A25 NOMe CO ₂ Et A25 NOMe CN A25 NOMe OMe A25 NOMe NH ₂ A25 NOMe NHMe A25 NOMe NEt ₂ A25 NOEt Me A25 NOEt CO ₂ Me A25 NOiPr Me A25 NOCH ₂ CH = CH ₂ Me A25 NOCH ₂ CH = CH ₂ Et A25 NOCH ₂ CH = CH ₂ CO ₂ Me A25 NOCH ₂ CH = CH ₂ CN A25 CHCN Me A25 C (CN) ₂ Me A25 C (CN) CO ₂ Et Me A25 NPh Me A26 NOMe Me A26 NOEt Me A26 NOCH ₂ CH = CH ₂ Me A26 NOMe CO ₂ Me A27 NOMe Me A27 NOEt Me A27 NOCH ₂ CH = CH ₂ Me A27 NOMe CO ₂ Me A28 NOMe Me A28 NOEt Me A28 NOCH ₂ CH = CH ₂ Me A28 NOMe CO ₂ Me A2 9 NOMe Me A29 NOEt Me A29 NOCH ₂ CH = CH ₂ Me A29 NOMe CO ₂ Me A30 NOMe Me A30 NOEt Me A30 NOCH ₂ CH = CH ₂ Me A30 NOMe CO ₂ Me A31 NOMe H A31 NOMe Me A31 NOMe Et A31 NOMe CO ₂ Me A31 NOMe CO ₂ Et A31 NOMe CN A31 NOMe OMe A31 NOMe NH ₂ A31 NOMe NHMe A31 NOMe NEt ₂ A31 NOEt Me A31 NOEt CO ₂ Me A31 NOiPr Me A31 NOCH ₂ CH = CH ₂ Me A31 NOCH ₂ CH = CH ₂ Et A31 NOCH ₂ CH = CH ₂ CO ₂ Me A31 NOCH ₂ CH = CH ₂ CN A31 CHCN Me A31 C (CN) ₂ Me A31 C (CN) CO ₂ Et Me A31 NPh Me A32 NOMe H A32 NOMe Me A32 NOMe Et A32 NOMe CO ₂ Me A32 NOMe CO ₂ Et A32 NOMe CN A32 NOMe OMe A32 NOMe NH ₂ A32 NOMe NHMe A32 NOMe NEt ₂ A32 NOEt Me A32 NOEt CO ₂ Me A32 NOiPr Me A32 NOCH ₂ CH = CH ₂ Me A32 NOCH ₂ CH = CH ₂ Et A32 NOCH ₂ CH = CH ₂ CO ₂ Me A32 NOCH ₂ CH = CH ₂ CN A32 CHCN Me A32 C (CN) ₂ Me A32 C (CN) CO ₂ Et Me A32 NPh Me A33 NOMe Me A33 NOEt Me A33 NOCH ₂ CH = CH ₂ Me A33 NOMe CO ₂ Me A34 NOMe Me A34 NOEt Me A34 NOCH ₂ CH = CH ₂ Me A34 NOMe CO ₂ Me A35 NOMe Me A35 NOEt Me A35 NOCH ₂ CH = CH ₂ Me A35 NOMe CO ₂ Me A36 NOMe Me A36 NOEt Me A36 NOCH ₂ CH = CH ₂ Me A36 NOMe CO ₂ Me A37 NOMe Me A37 NOEt Me A37 NOCH ₂ CH = CH ₂ Me A37 NOMe CO ₂ Me A38 NOMe Me A38 NOEt Me A38 NOCH ₂ CH = CH ₂ Me A38 NOMe CO ₂ Me A39 NOMe Me A39 NOEt Me A39 NOCH ₂ CH = CH ₂ Me A39 NOMe CO ₂ Me A40 NOMe Me A40 NOEt Me A40 NOCH ₂ CH = CH ₂ Me A40 NOMe CO ₂ Me A41 NOMe Me A41 NOEt Me A41 NOCH ₂ CH = CH ₂ Me A41 NOMe CO ₂ Me A41 NOMe CN A42 NOMe Me A42 NOEt Me A42 NOCH ₂ CH = CH ₂ Me A42 NOMe CO ₂ Me A42 NOMe CN A43 NOMe Me A43 NOEt Me A43 NOCH ₂ CH = CH ₂ Me A43 NOMe CO ₂ Me A44 NOMe Me A44 NOEt Me A44 NOCH ₂ CH = CH ₂ Me A44 NOMe CO ₂ Me A44 NOMe CN A45 NOMe H A45 NOMe Me A45 NOH Me A45 NOH Et A45 NOMe Et A45 NOMe iPr A45 NOMe nHex A45 NOMe CO ₂ Me A45 NOMe COMe A45 NOMe CO ₂ Et A45 NOMe CONHMe A45 NOMe CONMe ₂ A45 NOMe CN A45 NOMe OMe A45 NOMe OEt A45 NOMe SMe A45 NOMe NH ₂ A45 NOMe NHMe A45 NOMe NMe ₂ A45 NOMe NEt ₂ A45 NOMe CF ₃ A45 NOEt Me A45 NOEt Et A45 NOEt CO ₂ Me A45 NOnPr Me A45 NOnBu Me A45 NOnOct C (S) Me A45 NOiPr Me A45 NOCH ₂ CH = CH ₂ Me A45 NOCH ₂ CH = CH ₂ Et A45 NOCH ₂ CH = CH ₂ CO ₂ Me A45 NOCH ₂ CH = CH ₂ CO ₂ Et A45 CHCN Me A45 C (CN) ₂ Me A45 C (CN) CO ₂ Me Me A45 CHOMe Me A45 CHNO ₂ Me A45 NPh Me A45 N- (2-Pyridyl) Me A45 NOPh Me A45 NOC (O) Me Me A45 NOC (O) tBu Me A45 NOC (O) CF ₃ Me A45 NSMe Et A45 NCN Me A45 NOCF = CF ₂ Ph A45 NOC≡ CF cPr A45 NNO ₂ Me A45 NNO ₂ S (O) Me A45 NNMe ₂ Me A45 NNMe ₂ CO ₂ Me A45 NNMe ₂ SO ₂ Me A45 NS (O) Me C (S) NMe ₂ A45 NSO ₂ Me OC≡CF A45 NcHex 3-Pyridyl A45 NOMe 1-Piperidyl A45 NOMe 1-Imidazolyl A45 NOMe 1-Pyrazolinyl A45 NOMe 1-Morpholinyl A45 N- (1-Morpholinyl) Me A45 N- (1-Morpholinyl) CO ₂ Me A45 O Ph A45 O 3 -Pyridyl A45 O 1-Piperidyl A45 O 1-Imidazolyl A45 O 1-Pyrazolinyl A45 O 1-Morpholinyl A45 S Ph A45 S 3-Pyridyl A45 S 1-Piperidyl A45 S 1-Imidazolyl A45 S 1-Pyrazolinyl A45 S 1-Morpholinyl A46 NOMe Me A46 NOEt Me A46 NOCH ₂ CH = CH ₂ Me A46 NOMe CO ₂ Me A47 NOMe Me A47 NOEt Me A47 NOCH ₂ CH = CH ₂ Me A47 NOMe CO ₂ Me A48 NOMe Me A48 NOEt Me A48 NOCH ₂ CH = CH ₂ Me A48 NOMe CO ₂ Me A48 NOMe CN A49 NOMe Me A49 NOEt Me A49 NOCH ₂ CH = CH ₂ Me A49 NOMe CO ₂ Me A50 NOMe Me A50 NOEt Me A50 NOCH ₂ CH = CH ₂ Me A50 NOMe CO ₂ Me A51 NOMe Me A51 NOEt Me A51 NOCH ₂ CH = CH ₂ Me A51 NOMe CO ₂ Me A52 NOMe Me A52 NOEt Me A52 NOCH ₂ CH = CH ₂ Me A52 NOMe CO ₂ Me A53 NOMe Me A53 NOEt Me A53 NOCH ₂ CH = CH ₂ Me A53 NOMe CO ₂ Me A54 NOMe Me A54 NOEt Me A54 NOCH ₂ CH = CH ₂ Me A54 NOMe CO ₂ Me A55 NOMe Me A55 NOEt Me A55 NOCH ₂ CH = CH ₂ Me A55 NOMe CO ₂ Me A56 NOMe Me A56 NOEt Me A56 NOCH ₂ CH = CH ₂ Me A56 NOMe CO ₂ Me A57 NOMe Me A57 NOEt Me A57 NOCH ₂ CH = CH ₂ Me A57 NOMe CO ₂ Me ――――――――――――――――――――――――――

Table 3 shows compound groups AA2 to ZZ2.

Table 3

[0218]

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[0219]

[Table 3] ――――――――――――――――――――――――――― Compound group BR ¹ R ² ――――――――――― ―――――――――――――――――― AA2 HHH BB2 HMe H CC2 C (O) tBu HH DD2 C (O) tBu Me H EE2 C (O) tBu Cl H FF2 C ( O) tBu H Me GG2 C (O) Me HH HH2 C (O) Ph HH II2 C (O) CF ₃ HH JJ2 C (O) (3-Pyridyl) HH KK2 C (O) (2,6-Me ₂ -Ph) HH LL2 C (O) NMe ₂ HH MM2 C (O) NHPh HH NN2 Me HH OO2 CH ₂ OCH ₃ HH PP2 CH ₂ OCH ₂ CH ₃ HH QQ2 CH ₂ O (CH ₂ ) ₂ OCH ₃ HH RR2 CH ₂ SCH ₃ HH SS2 CH ₂ Ph HH TT2 C (O) OMe HH UU2 C (O) OEt HH VV2 P (O) (OEt) ₂ HH WW2 SO ₂ Me HH XX2 SO ₂ Ph HH YY2 SO ₂ NMe ₂ HH ZZ2 SO ₂ CF ₃ HH ―――――――――――――――――――――――――――――

Table 4 shows examples of combinations of the substituents A, X ² , X ³ and l in each of the compound groups AA2 to ZZ2.

[0221]

[Table 4] Table 4 ――――――――――――――――― AX ² X ³ l ――――――――――――――――― A1 CH ₂ O 1 A1 CH ₂ S 1 A1 CH ₂ NMe 1 A1 OO 1 A1 OO 2 A1 OS 1 A1 OS 2 A1 O NMe 1 A1 SO 1 A1 SS 1 A1 S NMe 1 A1 NMe O 1 A1 NMe S 1 A1 NMe NMe 3 A2 CH ₂ O 1 A2 CH ₂ S 1 A2 CH ₂ NMe 1 A2 OO 1 A2 OO 2 A2 OS 1 A2 OS 2 A2 O NMe 1 A2 SO 1 A2 SS 1 A2 S NMe 1 A2 NEt O 1 A2 NMe S 1 A3 CH ₂ CH ₂ 1 A3 CH ₂ O 1 A3 CH ₂ S 1 A3 CH ₂ NMe 1 A3 O CH ₂ 1 A3 OO 1 A3 OO 2 A3 OS 1 A3 OS 2 A3 O NMe 1 A3 S CH ₂ 1 A3 SO 1 A3 SS 1 A3 S NMe 1 A3 NMe CH ₂ 1 A3 NPh O 1 A3 NMe S 1 A4 CH ₂ CH ₂ 1 A4 CH ₂ O 1 A4 CH ₂ S 1 A4 CH ₂ NMe 1 A4 O CH ₂ 1 A4 OO 1 A4 OO 2 A4 OS 1 A4 OS 2 A4 O NMe 1 A4 S CH ₂ 1 A4 SO 1 A4 SS 1 A4 S NMe 1 A4 NMe CH ₂ 1 A4 NEt O 1 A4 NCO ₂ Me S 1 A5 CH ₂ S 1 A5 OS 2 A6 CH ₂ S 1 A6 OS 2 A7 CH ₂ S 1 A7 OS 2 A8 CH ₂ S 1 A8 OS 2 A9 CH ₂ S 1 A9 OO 2 A9 OS 2 A10 CH ₂ CH ₂ 1 A10 CH ₂ O 1 A10 CH ₂ S 1 A10 CH ₂ NMe 1 A10 O CH ₂ 1 A10 OO 1 A10 OO 2 A10 OS 1 A10 OS 2 A10 O NMe 1 A10 O NMe 2 A10 S CH ₂ 1 A10 SO 1 A10 SS 1 A10 S NMe 1 A10 NMe CH ₂ 1 A10 NMe O 1 A10 NH ₂ O 2 A10 NMe S 1 A10 NMe NMe 2 A11 CH ₂ O 1 A11 CH ₂ S 1 A11 CH ₂ NMe 1 A11 OO 1 A11 OO 2 A11 OS 1 A11 OS 2 A11 O NMe 1 A11 SO 1 A11 SS 1 A11 S NC (O) Ph 1 A11 NcPr O 1 A11 NC (O) Me S 1 A12 CH ₂ S 1 A12 OO 2 A12 OS 2 A13 CH ₂ S 1 A13 OS 2 A14 CH ₂ S 1 A14 OS 2 A15 CH ₂ S 1 A15 OS 2 A16 CH ₂ S 1 A16 OO 2 A16 OS 2 A17 CH ₂ S 1 A17 OO 2 A17 OS 2 A18 CH ₂ S 1 A18 OS 2 A19 CH ₂ S 1 A19 OO 2 A19 OS 2 A20 CH ₂ S 1 A20 OS 2 A21 CH ₂ S 1 A21 OS 2 A22 CH ₂ S 1 A22 OO 2 A22 OS 2 A23 CH ₂ S 1 A23 OO 2 A23 OS 2 A24 CH ₂ O 1 A24 CH ₂ S 1 A24 CH ₂ NMe 1 A24 OO 1 A24 OO 2 A24 OS 1 A24 OS 2 A24 O NMe 1 A24 SO 1 A24 SS 1 A24 S NnHex 1 A24 NcPr O 1 A24 NMe S 1 A25 CH ₂ O 1 A25 CH ₂ S 1 A25 CH ₂ NMe 1 A25 OO 1 A25 OO 2 A25 OS 1 A25 OS 2 A25 O NMe 1 A25 SO 1 A25 SS 1 A25 S NnHex 1 A25 NcPr O 1 A25 NMe S 1 A26 CH ₂ S 1 A26 OO 2 A26 OS 2 A27 CH ₂ S 1 A27 OS 2 A28 CH ₂ S 1 A28 OS 2 A29 CH ₂ S 1 A29 OS 2 A30 CH ₂ S 1 A30 OS 2 A31 CH ₂ O 1 A31 CH ₂ S 1 A31 CH ₂ NMe 1 A31 OO 1 A31 OO 2 A31 OS 1 A31 OS 2 A31 O NMe 1 A31 SO 1 A31 SS 1 A31 S NMe 1 A31 NMe O 1 A31 NMe S 1 A32 CH ₂ O 1 A32 CH ₂ S1 A32 CH ₂ NMe 1 A32 OO 1 A32 OO 2 A32 OS 1 A32 OS 2 A32 O NMe 1 A32 SO 1 A32 SS 1 A32 S NMe 1 A32 NMe O 1 A32 NMe S 1 A33 CH ₂ S 1 A33 OS 2 A34 CH ₂ S 1 A34 OS 2 A35 CH ₂ S 1 A35 OO 2 A35 OS 2 A36 CH ₂ S 1 A36 OS 2 A37 CH ₂ S 1 A37 OO 2 A37 OS 2 A38 CH ₂ S 1 A38 OS 2 A39 CH ₂ S 1 A39 OS 2 A40 CH ₂ S 1 A40 OS 2 A41 CH ₂ S 1 A41 OO 2 A41 OS 2 A42 CH ₂ S 1 A42 OO 2 A42 OS 2 A43 CH ₂ S 1 A43 OS 2 A44 CH ₂ S 1 A44 OO 2 A44 OS 2 A45 CH ₂ O 1 A45 CH ₂ S 1 A45 CH ₂ NMe 1 A45 OO 1 A45 OO 2 A45 OS 1 A45 OS 2 A45 O NMe 1 A45 SO 1 A45 SS 1 A45 S NMe 1 A45 NMe O 1 A45 NMe S 1 A46 CH ₂ S 1 A46 OS 2 A47 CH ₂ S 1 A47 OO 2 A47 OS 2 A48 CH ₂ S 1 A48 OS 2 A49 CH ₂ S 1 A49 OS 2 A50 CH ₂ S 1 A50 OS 2 A51 CH ₂ S 1 A51 OS 2 A52 CH ₂ S 1 A52 OS 2 A53 CH ₂ S 1 A53 OS 2 A54 CH ₂ S 1 A54 OS 2 A55 CH ₂ S 1 A55 OS 2 A56 CH ₂ S 1 A56 OS 2 A5 7 CH ₂ S 1 A57 OS 2 ―――――――――――――――――

The compound groups AA3 to ZZ3 are shown in Table 5.

Table 5

[0224]

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[0225]

[Table 5] ――――――――――――――――――――――――――― Compounds BR ¹ R ² ――――――――――― ―――――――――――――――――― AA3 HHH BB3 HMe H CC3 C (O) tBu HH DD3 C (O) tBu Me H EE3 C (O) tBu Cl H FF3 C ( O) tBu H Me GG3 C (O) Me HH HH3 C (O) Ph HH II3 C (O) CF ₃ HH JJ3 C (O) (3-Pyridyl) HH KK3 C (O) (2,6-Me ₂ -Ph) HH LL3 C (O) NMe ₂ HH MM3 C (O) NHPh HH NN3 Me HH OO3 CH ₂ OCH ₃ HH PP3 CH ₂ OCH ₂ CH ₃ HH QQ3 CH ₂ O (CH ₂ ) ₂ OCH ₃ HH RR3 CH ₂ SCH ₃ HH SS3 CH ₂ Ph HH TT3 C (O) OMe HH UU3 C (O) OEt HH VV3 P (O) (OEt) ₂ HH WW3 SO ₂ Me HH XX3 SO ₂ Ph HH YY3 SO ₂ NMe ₂ HH ZZ3 SO ₂ CF ₃ HH ―――――――――――――――――――――――――――――

Table 6 shows examples of combinations of the substituents A, X ² , X ³ , R ³ and l in each of the compound groups AA3 to ZZ3.

[0227]

[Table 6] Table 6 ―――――――――――――――――――― AX ² X ³ R ³ l ―――――――――――――――― ―――― A1 CH ₂ OH 1 A1 CH ₂ O Me 1 A1 CH ₂ OH 2 A1 CH ₂ O Me 2 A1 CH ₂ O nHex 1 A1 CH ₂ SH 1 A1 CH ₂ S Me 1 A1 CH ₂ S Me 2 A1 CH ₂ NMe H 1 A1 CH ₂ NMe Me 1 A1 CH ₂ NMe Me 2 A1 OOH 1 A1 OO Me 1 A1 OOH 2 A1 OO Me 2 A1 OSH 1 A1 OS Me 2 A1 O NCO ₂ Me H 1 A1 O NMe Me 1 A1 O NMe Me 2 A1 SSH 1 A1 SS Me 1 A1 SS Me 2 A1 S NC (O) Me H 1 A1 S NMe Me 1 A1 S NPh Me 2 A1 NMe NMe H 1 A1 NMe NMe Me 1 A1 NMe NcPr Me 2 A2 CH ₂ OH 1 A2 CH ₂ O Me 1 A2 CH ₂ OH 2 A2 CH ₂ O Me 2 A2 CH ₂ SH 1 A2 CH ₂ S Me 1 A2 CH ₂ S Me 2 A2 CH ₂ NMe H 1 A2 CH ₂ NMe Me 1 A2 CH ₂ NMe Me 2 A2 OOH 1 A2 OO Me 1 A2 OOH 2 A2 OO Me 2 A2 OSH 1 A2 OS Me 2 A2 O NMe H 1 A2 O NMe Me 1 A2 O NMe Me 2 A2 SSH 1 A2 SS Me 1 A2 SS Me 2 A2 S NCH ₂ OMe H 1 A2 S NMe Me 1 A2 S NMe Me 2 A2 NMe NMe H 1 A2 NMe NMe Me 1 A2 NMe NMe Me 2 A3 CH ₂ OH 1 A3 CH ₂ O Me 1 A3 CH ₂ OH 2 A3 CH ₂ O Me 2 A3 CH ₂ SH 1 A 3 CH ₂ S Me 1 A3 CH ₂ S Me 2 A3 CH ₂ NMe H 1 A3 CH ₂ NMe Me 1 A3 CH ₂ NMe Me 2 A3 OOH 1 A3 OO Me 1 A3 OOH 2 A3 OO Me 2 A3 OSH 1 A3 OS Me 2 A3 O NMe H 1 A3 O NMe Me 1 A3 O NMe Me 2 A3 SSH 1 A3 SS Me 1 A3 SS Me 2 A3 S NC (O) Ph H 1 A3 S NMe Me 1 A3 S NCH ₂ Ph Me 2 A3 NMe NCH = CH ₂ H1 A3 NMe NMe Me 1 A3 NMe NC≡CH Me 2 A4 CH ₂ OH 1 A4 CH ₂ O Me 1 A4 CH ₂ OH 2 A4 CH ₂ O Me 2 A4 CH ₂ SH 1 A4 CH ₂ S Me 1 A4 CH ₂ S Me 2 A4 CH ₂ NMe H 1 A4 CH ₂ NMe Me 1 A4 CH ₂ NMe Me 2 A4 OOH 1 A4 OO Me 1 A4 OOH 2 A4 OO Me 2 A4 OSH 1 A4 OS Me 2 A4 O NMe Me 1 A4 SSH 1 A4 SS Me 1 A4 SS Me 2 A4 S NMe Me 1 A4 NMe NMe Me 1 A5 CH ₂ OH 1 A5 OO Me 1 A6 CH ₂ OH 1 A6 OO Me 1 A7 CH ₂ OH 1 A7 OO Me 1 A8 CH ₂ OH 1 A8 OO Me 1 A9 CH ₂ OH 1 A9 CH ₂ O Me 1 A9 OO Me 1 A10 CH ₂ OH 0 A10 CH ₂ OH 1 A10 CH ₂ O Me 0 A10 CH ₂ O Me 1 A10 CH ₂ OH 2 A10 CH ₂ OH 3 A10 CH ₂ O Me 2 A10 CH ₂ O Et 1 A10 CH ₂ SH 1 A10 CH ₂ SH 2 A10 CH ₂ S Me 1 A10 CH ₂ S Me 2 A10 CH ₂ NH H 1 A10 CH ₂ NMe H 1 A10 CH ₂ NMe H 2 A10 CH ₂ NMe Me 1 A10 CH ₂ NMe Me 2 A10 OOH 1 A10 OO Me 1 A10 OOH 2 A10 OOH 3 A10 OO Me 2 A10 OSH 1 A10 OSH 2 A10 OS Me 1 A10 OS Me 2 A10 O NHH 1 A10 O NMe H 1 A10 O NMe H 2 A10 O NMe Me 1 A10 O NMe Me 2 A10 SSH 1 A10 SSH 2 A10 SS Me 1 A10 SS Me 2 A10 S NH H 1 A10 S NMe H 1 A10 S NMe H 2 A10 S NMe Me 1 A10 S NMe Me 2 A10 NMe NH H 1 A10 NMe NMe H 1 A10 NMe NMe H 2 A10 NMe NMe Me 1 A10 NMe NMe Me 2 A11 CH ₂ OH 1 A11 CH ₂ O Me 1 A11 CH ₂ OH 2 A11 CH ₂ O Me 2 A11 CH ₂ SH 1 A11 CH ₂ S Me 1 A11 CH ₂ S Me 2 A11 CH ₂ NMe H 1 A11 CH ₂ NMe Me 1 A11 CH ₂ NMe Me 2 A11 OOH 1 A11 OO Me 1 A11 OOH 2 A11 OO Me 2 A11 OSH 1 A11 OS Me 2 A11 O NMe Me 1 A11 SSH 1 A11 SS Me 1 A11 SS Me 2 A11 S NMe Me 1 A11 NMe NMe Me 1 A12 CH ₂ OH 1 A12 CH ₂ O Me 1 A12 OO Me 1 A13 CH ₂ OH 1 A13 OO Me 1 A14 CH ₂ OH 1 A14 OO Me 1 A15 CH ₂ OH 1 A15 OO Me 1 A16 CH ₂ OH 1 A16 CH ₂ O Me 1 A16 OO Me 1 A17 CH ₂ OH 1 A17 CH ₂ O Me 1 A17 OO Me 1 A18 CH ₂ OH 1 A18 OO Me 1 A19 CH ₂ OH 1 A19 CH ₂ O Me 1 A19 OO Me 1 A20 CH ₂ OH 1 A20 OO Me 1 A21 CH ₂ OH 1 A21 OO Me 1 A22 CH ₂ OH 1 A22 CH ₂ O Me 1 A22 OO Me 1 A23 CH ₂ OH 1 A23 CH ₂ O Me 1 A23 OO Me 1 A24 CH ₂ OH 1 A24 CH ₂ O Me 1 A24 CH ₂ OH 2 A24 CH ₂ O Me 2 A24 CH ₂ SH 1 A24 CH ₂ S Me 1 A24 CH ₂ NMe H 1 A24 CH ₂ NMe Me 1 A24 OOH 1 A24 OO M e 1 A24 OOH 2 A24 OO Me 2 A24 SS Me 1 A24 SS Me 2 A24 NMe NMe Me 1 A25 CH ₂ OH 1 A25 CH ₂ O Me 1 A25 CH ₂ OH 2 A25 CH ₂ O Me 2 A25 CH ₂ SH 1 A25 CH ₂ S Me 1 A25 CH ₂ NMe H 1 A25 CH ₂ NMe Me 1 A25 OOH 1 A25 OO Me 1 A25 OOH 2 A25 OO Me 2 A25 SS Me 1 A25 SS Me 2 A25 NMe NMe Me 1 A26 CH ₂ OH 1 A26 CH ₂ O Me 1 A26 OO Me 1 A27 CH ₂ OH 1 A27 OO Me 1 A28 CH ₂ OH 1 A28 OO Me 1 A29 CH ₂ OH 1 A29 OO Me 1 A30 CH ₂ OH 1 A30 OO Me 1 A31 CH ₂ OH 1 A31 CH ₂ O Me 1 A31 CH ₂ OH 2 A31 CH ₂ O Me 2 A31 CH ₂ SH 1 A31 CH ₂ S Me 1 A31 CH ₂ NMe H 1 A31 CH ₂ NMe Me 1 A31 OOH 1 A31 OO Me 1 A31 OOH 2 A31 OO Me 2 A31 SS Me 1 A31 SS Me 2 A31 NMe NMe Me 1 A32 CH ₂ OH 1 A32 CH ₂ O Me 1 A32 CH ₂ OH 2 A32 CH ₂ O Me 2 A32 CH ₂ SH 1 A32 CH ₂ S Me 1 A32 CH ₂ NMe H 1 A32 CH ₂ NMe Me 1 A32 OOH 1 A32 OO Me 1 A32 OOH 2 A32 OO Me 2 A32 SS Me 1 A32 SS Me 2 A32 NMe NMe Me 1 A33 CH ₂ OH 1 A33 OO Me 1 A34 CH ₂ OH 1 A34 OO Me 1 A35 CH ₂ OH 1 A35 CH ₂ O Me 1 A35 OO Me 1 A36 CH ₂ OH 1 A36 OO Me 1 A37 CH ₂ OH 1 A37 CH ₂ O Me 1 A37 OO Me 1 A38 CH ₂ OH 1 A38 OO Me 1 A39 CH ₂ OH 1 A39 OO Me 1 A40 CH ₂ OH 1 A40 OO Me 1 A41 CH ₂ OH 1 A41 CH ₂ O Me 1 A41 OO Me 1 A42 CH ₂ OH 1 A42 CH ₂ O Me 1 A42 OO Me 1 A43 CH ₂ OH 1 A43 OO Me 1 A44 CH ₂ OH 1 A44 CH ₂ O Me 1 A44 OO Me 1 A45 CH ₂ OH 1 A45 CH ₂ O Me 1 A45 CH ₂ OH 2 A45 CH ₂ O Me 2 A45 CH ₂ SH 1 A45 CH ₂ S Me 1 A45 CH ₂ NMe H 1 A45 CH ₂ NMe Me 1 A45 OOH 1 A45 OO Me 1 A45 OOH 2 A45 OO Me 2 A45 SS Me 1 A45 SS Me 2 A45 NMe NMe Me 1 A46 CH ₂ OH 1 A46 OO Me 1 A47 CH ₂ OH 1 A47 OO Me 1 A48 CH ₂ OH 1 A48 CH ₂ O Me 1 A48 OO Me 1 A49 CH ₂ OH 1 A49 OO Me 1 A50 CH ₂ OH 1 A50 OO Me 1 A51 CH ₂ OH 1 A51 OO Me 1 A52 CH ₂ OH 1 A52 OO Me 1 A53 CH ₂ OH 1 A53 OO Me 1 A54 CH ₂ OH 1 A54 OO Me 1 A55 CH ₂ OH 1 A55 OO Me 1 A56 CH ₂ OH 1 A56 OO Me 1 A57 CH ₂ OH 1 A57 OO Me 1 ――――――――――――――――――――

Table 7 shows the compound groups AA4 to ZZ4.

Table 7

[0230]

Embedded image

[0231]

[Table 7]

Table 8 shows examples of combinations of the substituents A, X, and Y in each of the compound groups AA4 to ZZ4.

[0233]

[Table 8] Table 8 ――――――――――――――――――――――― AXY ――――――――――――――――――― ---- A1 nOMe H A1 nOMe Me A1 nOMe Et A1 nOMe CO 2 Me A1 nOMe CO 2 Et A1 nOMe CN A1 nOMe OMe A1 nOMe NH 2 A1 nOMe NHMe A1 nOMe NMe 2 A1 NOEt Me A2 nOMe H A2 nOMe Me A2 NOMe Et A2 NOMe CO ₂ Me A2 NOMe CO ₂ Et A2 NOMe CN A2 NOMe OMe A2 NOMe NH ₂ A2 NOMe NHMe A2 NOMe NMe ₂ A2 NOEt Me A2 NOCH ₂ CH = CH ₂ Me A2 NOCH ₂ CH = CH ₂ Et A2 NOCH ₂ CH = CH ₂ CO ₂ Me A2 NOCH ₂ CH = CH ₂ CO ₂ Et A2 CHCN Me A2 C (CN) ₂ Me A2 CHOMe Me A2 NPh Me A3 NOMe H A3 NOMe Me A3 NOMe Et A3 NOMe CO ₂ Me A3 NOMe CO ₂ Et A3 NOMe CN A3 NOMe OMe A3 NOMe NH ₂ A3 NOMe NHMe A3 NOMe NEt ₂ A3 NOEt Me A3 NOEt CO ₂ Me A3 NOiPr Me A3 NOCH ₂ CH = CH ₂ Me A3 NOCH ₂ CH = CH ₂ Et A3 NOCH ₂ CH = CH ₂ CO ₂ Me A3 NOCH ₂ CH = CH ₂ CO ₂ nBu A3 CHCN Me A3 C (CN) ₂ Me A3 C (CN) CO ₂ Me Me A3 NPh Me A4 NOMe Me A4 NOMe Et A4 NOMe nHex A4 NOMe CO ₂ Me A4 NOMe CO ₂ Et A4 NOMe CN A4 NOMe OMe A4 NOMe NH ₂ A4 NOMe NHMe A4 NOMe NEt ₂ A4 NOnHex Me A4 NOCH ₂ CH = CH ₂ Me A4 NOCH ₂ CH = CH ₂ Et A4 NOCH ₂ CH = CH ₂ CO ₂ Me A4 NOCH ₂ CH = CH ₂ SMe A4 CHCN Me A4 C ( CN) ₂ Me A4 C (CN) CO ₂ Me Me A4 NPh Me A5 NOMe Me A5 NSMe Et A5 NCN COMe A6 CHCO ₂ Me CH = CH ₂ A6 NOCH = CH ₂ CF ₃ A6 NNO ₂ CH ₂ OMe A6 NNMe ₂ C (S) NHMe A7 NCH = CH ₂ OCH = CH ₂ A7 CHC≡CH OCF ₃ A7 NOCF ₃ OCH ₂ CH = CH ₂ A7 N- (1-Piperidyl) cHex A8 NOMe Me A8 NOC≡CH 1-Pyrazolyl A8 NCOPh C ≡CH A8 NOPh CO ₂ Me A9 NOMe Me A9 NCF ₃ OC≡CH A9 NOCONMe ₂ OCF = CF ₂ A9 NOEt CO ₂ Me A10 NOMe H A10 NOMe Me A10 NOH Me A10 NOH Et A10 NOMe Et A10 NOMe iPr A10 NOMe nHex A10 NOMe CO ₂ Me A10 NOMe COMe A10 NOMe CO ₂ Et A10 NOMe CONHMe A10 NOMe CONMe ₂ A10 NOMe CN A10 NOMe OMe A10 NOMe OEt A10 NOMe SMe A10 NOMe NH ₂ A10 NOMe NHMe A10 NOMe NMe ₂ A10 NOMe NEt ₂ A10 NOMe CF ₃ A10 NOEt Me A10 NOEt Et A10 NOEt CO ₂ Me A10 NOnPr Me A10 NOnBu Me A10 NOnOct C (S) Me A10 NOiPr Me A10 NOCH ₂ CH = CH ₂ Me A10 NOCH ₂ CH = CH ₂ Et A10 NOCH ₂ CH = CH ₂ CO ₂ Me A10 NOCH ₂ CH = CH ₂ CO ₂ Et A 10 CHCN Me A10 C (CN) ₂ Me A10 C (CN) CO ₂ Me Me A10 CHOMe Me A10 CHNO ₂ Me A10 NPh Me A10 N- (2-Pyridyl) Me A10 NOPh Me A10 NOC (O) Me Me A10 NOC (O) tBu Me A10 NOC (O) CF ₃ Me A10 NSMe Et A10 NCN Me A10 NOCF = CF ₂ Ph A10 NOC≡CF cPr A10 NNO ₂ Me A10 NNO ₂ S (O) Me A10 NNMe ₂ Me A10 NNMe ₂ CO ₂ Me A10 NNMe ₂ SO ₂ Me A10 NS (O) Me C (S) NMe ₂ A10 NSO ₂ Me OC≡CF A10 NcHex 3-Pyridyl A10 NCH ₂ OMe 1-Piperidyl A10 NCOMe 1-Imidazolyl A10 NCOCF ₃ 1-Pyrazolinyl A10 NCO ₂ Me 1-Morpholinyl A10 N- (1-Morpholinyl) Me A10 N- (1-Morpholinyl) CO ₂ Me A10 O Ph A10 O 3-Pyridyl A10 O 1-Piperidyl A10 O 1-Imidazolyl A10 O 1-Pyrazolinyl A10 O 1-Morpholinyl A10 S Ph A10 S 3-Pyridyl A10 S 1-Piperidyl A10 S 1-Imidazolyl A10 S 1-Pyrazolinyl A10 S 1-Morpholinyl A11 NOMe H A11 NOMe Me A11 NOMe Et A11 NOMe CO ₂ Me A11 NOMe CO ₂ Et A11 NOMe CN A11 NOMe OMe A11 NOMe NH ₂ A11 NOMe NHMe A11 NOMe NEt ₂ A11 NOEt Me A11 NOEt CO ₂ Me A11 NOiPr Me A11 NOCH ₂ CH = CH ₂ Me A11 NOCH ₂ CH = CH ₂ Et A11 NOCH ₂ CH = CH ₂ CO ₂ Me A11 CHCN Me A11 C (C N) ₂ Me A11 C (CN) CO ₂ Me Me A11 NPh Me A12 NOMe H A12 NOMe Me A12 NOMe Et A12 NOMe CO ₂ Me A12 NOMe CO ₂ Et A12 NOMe CN A12 NOMe OMe A12 NOMe NH ₂ A12 NOMe NHMe A12 NOMe NEt ₂ A12 NOEt Me A12 NOEt CO ₂ Me A12 NOiPr Me A12 NOCH ₂ CH = CH ₂ Me A12 NOCH ₂ CH = CH ₂ Et A12 NOCH ₂ CH = CH ₂ CO ₂ Me A12 CHCN Me A12 C (CN) ₂ Me A12 C (CN) CO ₂ Me Me A13 NOMe Me A13 NOEt Et A13 NOCH ₂ CH = CH ₂ Me A13 NOMe CO ₂ Me A14 NOMe Me A14 NOEt Me A14 NOCH ₂ CH = CH ₂ Me A14 NOMe CO ₂ Me A15 NOMe Me A15 NOEt Me A15 NOCH ₂ CH = CH ₂ iPr A15 NOMe CO ₂ Me A16 NOMe Me A16 NOEt Me A16 NOCH ₂ CH = CH ₂ NEt ₂ A16 NOMe CONHMe A17 NOMe Me A17 NOEt Me A17 NOCH ₂ CH = CH ₂ NEt ₂ A17 NOPh CONHMe A18 NOMe Me A18 NOEt Me A18 NOCH ₂ CH = CH ₂ NEt ₂ A18 NOC (O) tBu OnBu A19 NOMe Me A19 NOEt Me A19 NOCH ₂ CH = CH ₂ NnPr ₂ A19 NOMe OiPr A20 NOMe Me A20 NOEt Me A20 NOCH ₂ CH = CH ₂ COnBu A20 NSnBu OtBu A21 NOMe Me A21 NOEt Me A21 NOCH ₂ CH = CH ₂ CONHEt A21 NOtBu Me A22 NOMe Me A22 NOEt Me A22 NOCH ₂ CH = CH ₂ Me A22 NOMe CO ₂ Me A23 NOMe Me A23 NOEt M _{e A23 NOCH 2 CH = CH 2} Me A23 NOMe CO 2 Me A24 NOMe H A24 NOMe Me A24 NOMe Et A24 NOMe CO 2 Me A24 NOMe CO 2 Et A24 NOMe CN A24 NOMe OMe A24 NOMe NH 2 A24 NOMe NHMe A24 NOMe NEt 2 A24 NOEt Me A24 NOEt CO ₂ Me A24 NOiPr Me A24 NOCH ₂ CH = CH ₂ Me A24 NOCH ₂ CH = CH ₂ Et A24 NOCH ₂ CH = CH ₂ CO ₂ Me A24 NOCH ₂ CH = CH ₂ CO ₂ nBu A24 CHCN Me A24 C (CN) ₂ Me A24 C (CN) CO ₂ Me Me A24 NPh Me A25 NOMe H A25 NOMe Me A25 NOMe Et A25 NOMe CO ₂ Me A25 NOMe CO ₂ Et A25 NOMe CN A25 NOMe OMe A25 NOMe NH ₂ A25 NOMe NHMe A25 NOMe NEt ₂ A25 NOEt Me A25 NOEt CO ₂ Me A25 NOiPr Me A25 NOCH ₂ CH = CH ₂ Me A25 NOCH ₂ CH = CH ₂ Et A25 NOCH ₂ CH = CH ₂ CO ₂ Me A25 NOCH ₂ CH = CH ₂ CN A25 CHCN Me A25 C (CN) ₂ Me A25 C (CN) CO ₂ Et Me A25 NPh Me A26 NOMe Me A26 NOEt Me A26 NOCH ₂ CH = CH ₂ Me A26 NOMe CO ₂ Me A27 NOMe Me A27 NOEt Me A27 NOCH ₂ CH = CH ₂ Me A27 NOMe CO ₂ Me A28 NOMe Me A28 NOEt Me A28 NOCH ₂ CH = CH ₂ Me A28 NOMe CO ₂ Me A29 NOMe Me A29 NOEt Me A29 NOCH ₂ CH = CH ₂ Me A29 NOMe CO ₂ Me A30 NOMe Me A30 NOEt Me A30 NOCH ₂ CH = CH ₂ Me A30 NOMe CO ₂ Me A31 NOMe H A31 NOMe Me A31 NOMe Et A31 NOMe CO ₂ Me A31 NOMe CO ₂ Et A31 NOMe CN A31 NOMe OMe A31 NOMe NH ₂ A31 NOMe NHMe A31 NOMe NEt ₂ A31 NOEt Me A31 NOEt CO ₂ Me A31 NOiPr Me A31 NOCH ₂ CH = CH ₂ Me A31 NOCH ₂ CH = CH ₂ Et A31 NOCH ₂ CH = CH ₂ CO ₂ Me A31 NOCH ₂ CH = CH ₂ CN A31 CHCN Me A31 C (CN) ₂ Me A31 C (CN) CO ₂ Et Me A31 NPh Me A32 NOMe H A32 NOMe Me A32 NOMe Et A32 NOMe CO ₂ Me A32 NOMe CO ₂ Et A32 NOMe CN A32 NOMe OMe A32 NOMe NH ₂ A32 NOMe NHMe A32 NOMe NEt ₂ A32 NOEt Me A32 NOEt CO ₂ Me A32 NOiPr Me A32 NOCH ₂ CH = CH ₂ Me A32 NOCH ₂ CH = CH ₂ Et A32 NOCH ₂ CH = CH ₂ CO ₂ Me A32 NOCH ₂ CH = CH ₂ CN A32 CHCN Me A32 C (CN) ₂ Me A32 C (CN) CO ₂ Et Me A32 NPh Me A33 NOMe Me A33 NOEt Me A33 NOCH ₂ CH = CH ₂ Me A33 NOMe CO ₂ Me A34 NOMe Me A34 NOEt Me A34 NOCH ₂ CH = CH ₂ Me A34 NOMe CO ₂ Me A35 NOMe Me A35 NOEt Me A35 NOCH ₂ CH = CH ₂ Me A35 NOMe CO ₂ Me A36 NOMe Me A36 NOEt Me A36 NOCH ₂ CH = CH ₂ Me A36 NOMe CO ₂ Me A37 NOMe Me A37 NOEt Me A37 NOCH ₂ CH = CH ₂ Me A37 NOMe CO ₂ Me A38 NOMe Me A38 NOEt Me A38 NOCH ₂ CH = CH ₂ Me A38 NOMe CO ₂ Me A39 NOMe Me A39 NOEt Me A39 NOCH ₂ CH = CH ₂ Me A39 NOMe CO ₂ Me A40 NOMe Me A40 NOEt Me A40 NOCH ₂ CH = CH ₂ Me A40 NOMe CO ₂ Me A41 NOMe Me A41 NOEt Me A41 NOCH ₂ CH = CH ₂ Me A41 NOMe CO ₂ Me A41 NOMe CN A42 NOMe Me A42 NOEt Me A42 NOCH ₂ CH = CH ₂ Me A42 NOMe CO ₂ Me A42 NOMe CN A43 NOMe Me A43 NOEt Me A43 NOCH ₂ CH = CH ₂ Me A43 NOMe CO ₂ Me A44 NOMe Me A44 NOEt Me A44 NOCH ₂ CH = CH ₂ Me A44 NOMe CO ₂ Me A44 NOMe CN A45 NOMe H A45 NOMe Me A45 NOH Me A45 NOH Et A45 NOMe Et A45 NOMe iPr A45 NOMe nHex A45 NOMe CO ₂ Me A45 NOMe COMe A45 NOMe CO ₂ Et A45 NOMe CONHMe A45 NOMe CONMe ₂ A45 NOMe CN A45 NOMe OMe A45 NOMe OEt A45 NOMe SMe A45 NOMe NH ₂ A45 NOMe NHMe A45 NOMe NMe ₂ A45 NOMe NEt ₂ A45 NOMe CF ₃ A45 NOEt Me A45 NOEt Et A45 NOEt CO ₂ Me A45 NOnPr Me A45 NOnBu Me A45 NOnOct C (S) Me A45 NOiPr Me A45 NOCH ₂ CH = CH ₂ Me A45 NOCH ₂ CH = CH ₂ Et A45 NOCH ₂ CH = CH ₂ CO ₂ Me A45 NOCH ₂ CH = CH ₂ CO ₂ Et A45 CHCN Me A45 C (CN) ₂ Me A45 C (CN) CO ₂ M e Me A45 CHOMe Me A45 CHNO ₂ Me A45 NPh Me A45 N- (2-Pyridyl) Me A45 NOPh Me A45 NOC (O) Me Me A45 NOC (O) tBu Me A45 NOC (O) CF ₃ Me A45 NSMe Et A45 NCN Me A45 NOCF = CF ₂ Ph A45 NOC≡CF cPr A45 NNO ₂ Me A45 NNO ₂ S (O) Me A45 NNMe ₂ Me A45 NNMe ₂ CO ₂ Me A45 NNMe ₂ SO ₂ Me A45 NS (O) Me C (S ) NMe ₂ A45 NSO ₂ Me OC≡CF A45 NcHex 3-Pyridyl A45 NOMe 1-Piperidyl A45 NOMe 1-Imidazolyl A45 NOMe 1-Pyrazolinyl A45 NOMe 1-Morpholinyl A45 N- (1-Morpholinyl) Me A45 N- (1- Morpholinyl) CO ₂ Me A45 O Ph A45 O 3-Pyridyl A45 O 1-Piperidyl A45 O 1-Imidazolyl A45 O 1-Pyrazolinyl A45 O 1-Morpholinyl A45 S Ph A45 S 3-Pyridyl A45 S 1-Piperidyl A45 S 1- Imidazolyl A45 S 1-Pyrazolinyl A45 S 1-Morpholinyl A46 NOMe Me A46 NOEt Me A46 NOCH ₂ CH = CH ₂ Me A47 NOMe Me A47 NOEt Me A47 NOCH ₂ CH = CH ₂ Me A47 NOMe CO ₂ Me A48 NOMe Me A48 NOEt Me A48 NOCH ₂ CH = CH ₂ Me A48 NOMe CN A49 NOEt Me A49 NOCH ₂ CH = CH ₂ Me A49 NOMe CO ₂ Me A50 NOEt Me A50 NOCH ₂ CH = CH ₂ Me A50 NOMe CO ₂ Me A51 NOEt Me A51 NOCH ₂ CH = CH ₂ Me A51 NOMe CO ₂ Me A52 NOEt Me A52 NOCH ₂ CH = CH ₂ Me A52 NOMe CO ₂ Me A53 NOEt Me A53 NOCH ₂ CH = CH ₂ Me A53 NOMe CO ₂ Me A54 NOEt Me A54 NOCH ₂ CH = CH ₂ Me A54 NOMe CO ₂ Me A55 NOEt Me A55 NOCH ₂ CH = CH ₂ Me A55 NOMe CO ₂ Me A56 NOEt Me A56 NOCH ₂ CH = CH ₂ Me A56 NOMe CO ₂ Me A57 NOEt Me A57 NOCH ₂ CH = CH ₂ Me A57 NOMe CO ₂ Me ――――― ――――――――――――――――――

Table 9 shows compound groups AA5 to ZZ5.

Table 9

[0236]

Embedded image

[0237]

[Table 9]

Table 10 shows examples of combinations of the substituents A, X ² , X ³ and 1 in each of the compound groups AA5 to ZZ5.

[0239]

[Table 10] Table 10 ――――――――――――――――― AX ² X ³ l ――――――――――――――――― A1 CH ₂ O 1 A1 CH ₂ S 1 A1 CH ₂ NMe 1 A1 OO 1 A1 OO 2 A1 OS 1 A1 OS 2 A1 O NMe 1 A1 SO 1 A1 SS 1 A1 S NMe 1 A1 NMe O 1 A1 NMe S 1 A1 NMe NMe 3 A2 CH ₂ O 1 A2 CH ₂ S 1 A2 CH ₂ NMe 1 A2 OO 1 A2 OO 2 A2 OS 1 A2 OS 2 A2 O NMe 1 A2 SO 1 A2 SS 1 A2 S NMe 1 A2 NMe CH ₂ 1 A2 NEt O 1 A2 NMe S 1 A3 CH ₂ O 1 A3 CH ₂ S 1 A3 CH ₂ NMe 1 A3 OO 1 A3 OO 2 A3 OS 1 A3 OS 2 A3 O NMe 1 A3 SO 1 A3 SS 1 A3 S NMe 1 A3 NPh O 1 A3 NMe S 1 A4 CH ₂ O 1 A4 CH ₂ S1 A4 CH ₂ NMe 1 A4 OO 1 A4 OO 2 A4 OS 1 A4 OS 2 A4 O NMe 1 A4 SO 1 A4 SS 1 A4 S NMe 1 A4 NEt O 1 A4 NCO2Me S 1 A5 CH ₂ S 1 A5 OS 2 A6 CH ₂ S 1 A6 OS 2 A7 CH ₂ S 1 A7 OS 2 A8 CH ₂ S 1 A8 OO 2 A8 OS 2 A9 CH ₂ S 1 A9 OO 2 A9 OS 2 A10 CH ₂ CH ₂ 1 A10 CH ₂ O 1 A10 CH ₂ S 1 A10 CH ₂ NMe 1 A10 O CH ₂ 1 A10 OO 1 A10 OO 2 A10 OS 1 A10 OS 2 A10 O NMe 1 A10 O NMe 2 A10 S CH ₂ 1 A10 SO 1 A10 SS 1 A10 S NMe 1 A10 NMe CH ₂ 1 A10 NMe O 1 A10 NH ₂ O 2 A10 NMe S 1 A10 NMe NMe 2 A11 CH ₂ O 1 A11 CH ₂ S 1 A11 CH ₂ NMe 1 A11 OO 1 A11 OO 2 A11 OS 1 A11 OS 2 A11 O NMe 1 A11 SO 1 A11 SS 1 A11 S NC (O) Ph 1 A11 NcPr O 1 A11 NC (O) Me S 1 A12 CH ₂ S 1 A12 OO 2 A12 OS 2 A13 CH ₂ S 1 A13 OS 2 A14 CH ₂ S 1 A14 OS 2 A15 CH ₂ S 1 A15 OS 2 A16 CH ₂ S 1 A16 OO 2 A16 OS 2 A17 CH ₂ S 1 A17 OO 2 A17 OS 2 A18 CH ₂ S 1 A18 OO 2 A18 OS 2 A19 CH ₂ S 1 A19 OO 2 A19 OS 2 A20 CH ₂ S 1 A20 OS 2 A21 CH ₂ S 1 A21 OS 2 A22 CH ₂ S 1 A22 OO 2 A22 OS 2 A23 CH ₂ S 1 A23 OO 2 A23 OS 2 A24 CH ₂ O 1 A24 CH ₂ S 1 A24 CH ₂ NMe 1 A24 OO 1 A24 OO 2 A24 OS 1 A24 OS 2 A24 O NMe 1 A24 SO 1 A24 SS 1 A24 S NnHex 1 A24 NcPr O 1 A24 NMe S 1 A25 CH ₂ O 1 A25 CH ₂ S 1 A25 CH ₂ NMe 1 A25 OO 1 A25 OO 2 A25 OS 1 A25 OS 2 A25 O NMe 1 A25 S CH ₂ 1 A25 SO 1 A25 SS 1 A25 S NnHex 1 A25 NcPr O 1 A25 NMe S 1 A26 CH ₂ S 1 A26 OO 2 A26 OS 2 A27 CH ₂ S 1 A27 OS 2 A28 CH ₂ S 1 A28 OS 2 A29 CH ₂ S 1 A29 OS 2 A30 CH ₂ S 1 A30 OS 2 A31 CH ₂ O 1 A31 CH ₂ S 1 A31 CH ₂ NMe 1 A31 OO 1 A31 OO 2 A31 OS 1 A31 OS 2 A31 O NMe 1 A31 SO 1 A31 SS 1 A31 S NMe 1 A31 NMe O 1 A31 NMe S 1 A32 CH ₂ O 1 A32 CH ₂ S 1 A32 CH ₂ NMe 1 A32 OO 1 A32 OO 2 A32 OS 1 A32 OS 2 A32 O NMe 1 A32 SO 1 A32 SS 1 A32 S NMe 1 A32 NMe O 1 A32 NMe S 1 A33 CH ₂ S 1 A33 OS 2 A34 CH ₂ S 1 A34 OS 2 A35 CH ₂ S 1 A35 OO 2 A35 OS 2 A36 CH ₂ S 1 A36 OS 2 A37 CH ₂ S 1 A37 OO 2 A37 OS 2 A38 CH ₂ S 1 A38 OS 2 A39 CH ₂ S 1 A39 OS 2 A40 CH ₂ S 1 A40 OS 2 A41 CH ₂ S 1 A41 OO 2 A41 OS 2 A42 CH ₂ S 1 A42 OO 2 A42 OS 2 A43 CH ₂ S 1 A43 OO 2 A43 OS 2 A44 CH ₂ S 1 A44 OO 2 A44 OS 2 A45 CH ₂ O 1 A45 CH ₂ S 1 A45 CH ₂ NMe 1 A45 OO 1 A45 OO 2 A45 OS 1 A45 OS 2 A45 O NMe 1 A45 SO 1 A45 SS 1 A45 S NMe 1 A45 NMe O 1 A45 NMe S 1 A46 CH ₂ S 1 A46 OS 2 A47 CH ₂ S 1 A47 OS 2 A48 CH ₂ S 1 A48 OO 2 A48 OS 2 A49 CH ₂ S 1 A49 OS 2 A50 CH ₂ S 1 A50 OS 2 A51 CH ₂ S 1 A51 OS 2 A52 CH ₂ S 1 A52 OS 2 A53 CH ₂ S 1 A53 OS 2 A54 CH ₂ S 1 A54 OS 2 A55 CH ₂ S 1 A55 OS 2 A56 CH ₂ S 1 A56 OS 2 A57 CH ₂ S 1 A57 OS 2 ―――――――――――――――――

The compound groups AA6 to ZZ6 are shown in Table 11.

Table 11

[0242]

Embedded image

[0243]

[Table 11]

Table 12 shows examples of combinations of the substituents A, X ² , X ³ , R ³ and 1 in each of the compound groups AA6 to ZZ6.

[0245]

[Table 12] Table 12 ―――――――――――――――――――― AX ² X ³ R ³ l ―――――――――――――――― ―――― A1 CH ₂ OH 1 A1 CH ₂ O Me 1 A1 CH ₂ OH 2 A1 CH ₂ O Me 2 A1 CH ₂ O nHex 1 A1 CH ₂ SH 1 A1 CH ₂ S Me 1 A1 CH ₂ S Me 2 A1 CH ₂ NMe H 1 A1 CH ₂ NMe Me 1 A1 CH ₂ NMe Me 2 A1 OOH 1 A1 OO Me 1 A1 OOH 2 A1 OO Me 2 A1 OSH 1 A1 OS Me 2 A1 O NCO ₂ Me H 1 A1 O NMe Me 1 A1 O NMe Me 2 A1 SSH 1 A1 SS Me 1 A1 SS Me 2 A1 S NC (O) Me H 1 A1 S NMe Me 1 A1 S NPh Me 2 A1 NMe NMe H 1 A1 NMe NMe Me 1 A1 NMe NcPr Me 2 A2 CH ₂ OH 1 A2 CH ₂ O Me 1 A2 CH ₂ OH 2 A2 CH ₂ O Me 2 A2 CH ₂ SH 1 A2 CH ₂ S Me 1 A2 CH ₂ S Me 2 A2 CH ₂ NMe H 1 A2 CH ₂ NMe Me 1 A2 CH ₂ NMe Me 2 A2 OOH 1 A2 OO Me 1 A2 OOH 2 A2 OO Me 2 A2 OSH 1 A2 OS Me 2 A2 O NMe H 1 A2 O NMe Me 1 A2 O NMe Me 2 A2 SSH 1 A2 SS Me 1 A2 SS Me 2 A2 S NCH ₂ OMe H 1 A2 S NMe Me 1 A2 S NMe Me 2 A2 NMe NMe H 1 A2 NMe NMe Me 1 A2 NMe NMe Me 2 A3 CH ₂ OH 1 A3 CH ₂ O Me 1 A3 CH ₂ OH 2 A3 CH ₂ O Me 2 A3 CH ₂ SH 1 A3 CH ₂ S Me 1 A3 CH ₂ S Me 2 A3 CH ₂ NMe H 1 A3 CH ₂ NMe Me 1 A3 CH ₂ NMe Me 2 A3 OOH 1 A3 OO Me 1 A3 OOH 2 A3 OO Me 2 A3 OSH 1 A3 OS Me 2 A3 O NMe H 1 A3 O NMe Me 1 A3 O NMe Me 2 A3 SSH 1 A3 SS Me 1 A3 SS Me 2 A3 S NC (O) Ph H 1 A3 S NMe Me 1 A3 S NCH ₂ Ph Me 2 A3 NMe NCH = CH ₂ H 1 A3 NMe NMe Me 1 A3 NMe NC≡CH Me 2 A4 CH ₂ OH 1 A4 CH ₂ O Me 1 A4 CH ₂ OH 2 A4 CH ₂ O Me 2 A4 CH ₂ SH 1 A4 CH ₂ S Me 1 A4 CH ₂ S Me 2 A4 CH ₂ NMe H 1 A4 CH ₂ NMe Me 1 A4 CH ₂ NMe Me 2 A4 OOH 1 A4 OO Me 1 A4 OOH 2 A4 OO Me 2 A4 OSH 1 A4 OS Me 2 A4 O NMe Me 1 A4 SSH 1 A4 SS Me 1 A4 SS Me 2 A4 S NMe Me 1 A4 NMe NMe Me 1 A5 CH ₂ OH 1 A5 OO Me 1 A6 CH ₂ OH 1 A6 OO Me 1 A7 CH ₂ OH 1 A7 OO Me 1 A8 CH ₂ OH 1 A8 OO Me 1 A9 CH ₂ OH 1 A9 CH ₂ O Me 1 A9 OO Me 1 A10 CH ₂ OH 0 A10 CH ₂ OH 1 A10 CH ₂ O Me 0 A10 CH ₂ O Me 1 A10 CH ₂ OH 2 A10 CH ₂ OH 3 A10 CH ₂ O Me 2 A10 CH ₂ O Et 1 A10 CH ₂ SH 1 A10 CH ₂ SH 2 A10 CH ₂ S Me 1 A10 CH ₂ S Me 2 A10 CH ₂ NH H 1 A10 CH ₂ NMe H 1 A10 CH ₂ NMe H 2 A10 CH ₂ NMe Me 1 A10 CH ₂ N Me Me 2 A10 OOH 1 A10 OO Me 1 A10 OOH 2 A10 OOH 3 A10 OO Me 2 A10 OSH 1 A10 OSH 2 A10 OS Me 1 A10 OS Me 2 A10 O NH H 1 A10 O NMe H 1 A10 O NMe H 2 A10 O NMe Me 1 A10 O NMe Me 2 A10 SSH 1 A10 SSH 2 A10 SS Me 1 A10 SS Me 2 A10 S NHH 1 A10 S NMe H 1 A10 S NMe H 2 A10 S NMe Me 1 A10 S NMe Me 2 A10 NMe NH H 1 A10 NMe NMe H 1 A10 NMe NMe H 2 A10 NMe NMe Me 1 A10 NMe NMe Me 2 A11 CH ₂ OH 1 A11 CH ₂ O Me 1 A11 CH ₂ OH 2 A11 CH ₂ O Me 2 A11 CH ₂ SH 1 A11 CH ₂ S Me 1 A11 CH ₂ S Me 2 A11 CH ₂ NMe H 1 A11 CH ₂ NMe Me 1 A11 CH ₂ NMe Me 2 A11 OOH 1 A11 OO Me 1 A11 OOH 2 A11 OO Me 2 A11 OSH 1 A11 OS Me 2 A11 O NMe Me 1 A11 SSH 1 A11 SS Me 1 A11 SS Me 2 A11 S NMe Me 1 A11 NMe NMe Me 1 A12 CH ₂ OH 1 A12 CH ₂ O Me 1 A12 OO Me 1 A13 CH ₂ OH 1 A13 OO Me 1 A14 CH ₂ OH 1 A14 OO Me 1 A15 CH ₂ OH 1 A15 CH ₂ OH 1 A16 CH ₂ O Me 1 A16 OO Me 1 A17 CH ₂ OH 1 A17 CH ₂ O Me 1 A17 OO Me 1 A18 CH ₂ OH 1 A18 OO Me 1 A19 CH ₂ OH 1 A19 CH ₂ O Me 1 A19 OO Me 1 A20 CH ₂ OH 1 A20 OO Me 1 A21 CH ₂ OH 1 A21 OO Me 1 A22 CH ₂ OH 1 A22 CH ₂ O Me 1 A22 OO Me 1 A23 CH ₂ OH 1 A23 CH ₂ O Me 1 A23 OO Me 1 A24 CH ₂ OH 1 A24 CH ₂ O Me 1 A24 CH ₂ OH 2 A24 CH ₂ O Me 2 A24 CH ₂ SH 1 A24 CH ₂ SMe 1 A24 CH ₂ NMe H 1 A24 CH ₂ NMe Me 1 A24 OOH 1 A24 OO Me 1 A24 OOH 2 A24 OO Me 2 A24 SS Me 1 A24 SS Me 2 A24 NMe NMe Me 1 A25 CH ₂ OH 1 A25 CH ₂ O Me 1 A25 CH ₂ OH 2 A25 CH ₂ O Me 2 A25 CH ₂ SH 1 A25 CH ₂ S Me 1 A25 CH ₂ NMe H 1 A25 CH ₂ NMe Me 1 A25 OOH 1 A25 OO Me 1 A25 OOH 2 A25 OO Me 2 A25 SS Me 1 A25 SS Me 2 A25 NMe NMe Me 1 A26 CH ₂ OH 1 A26 CH ₂ O Me 1 A26 OO Me 1 A27 CH ₂ OH 1 A27 OO Me 1 A28 CH ₂ OH 1 A28 OO Me 1 A29 CH ₂ OH 1 A29 OO Me 1 A30 CH ₂ OH 1 A30 OO Me 1 A31 CH ₂ OH 1 A31 CH ₂ O Me 1 A31 CH ₂ OH 2 A31 CH ₂ O Me 2 A31 CH ₂ SH 1 A31 CH ₂ SMe 1 A31 CH ₂ NMe H 1 A31 CH ₂ NMe Me 1 A31 OOH 1 A31 OO Me 1 A31 OOH 2 A31 OO Me 2 A31 SS Me 1 A31 SS Me 2 A31 NMe NMe Me 1 A32 CH ₂ OH 1 A32 CH ₂ O Me 1 A32 CH ₂ OH 2 A32 CH ₂ O Me 2 A32 CH ₂ SH 1 A32 CH ₂ S Me 1 A32 CH ₂ NMe H 1 A32 CH ₂ NMe Me 1 A32 OOH 1 A3 2 OO Me 1 A32 OOH 2 A32 OO Me 2 A32 SS Me 1 A32 SS Me 2 A32 NMe NMe Me 1 A33 CH ₂ OH 1 A33 OO Me 1 A34 CH ₂ OH 1 A34 OO Me 1 A35 CH ₂ OH 1 A35 OO Me 1 A36 CH ₂ OH 1 A36 OO Me 1 A37 CH ₂ OH 1 A37 CH ₂ O Me 1 A37 OO Me 1 A38 CH ₂ OH 1 A38 OO Me 1 A39 CH ₂ OH 1 A39 OO Me 1 A40 CH ₂ OH 1 A40 OO Me 1 A41 CH ₂ OH 1 A41 CH ₂ O Me 1 A41 OO Me 1 A42 CH ₂ OH 1 A42 CH ₂ O Me 1 A42 OO Me 1 A43 CH ₂ OH 1 A43 OO Me 1 A44 CH ₂ OH 1 A44 CH ₂ O Me 1 A44 OO Me 1 A45 CH ₂ OH 1 A45 CH ₂ O Me 1 A45 CH ₂ OH 2 A45 CH ₂ O Me 2 A45 CH ₂ SH 1 A45 CH ₂ S Me 1 A45 CH ₂ NMe H 1 A45 CH ₂ NMe Me 1 A45 OOH 1 A45 OO Me 1 A45 OOH 2 A45 OO Me 2 A45 SS Me 1 A45 SS Me 2 A45 NMe NMe Me 1 A46 CH ₂ OH 1 A46 OO Me 1 A47 CH ₂ OH 1 A47 OO Me 1 A48 CH ₂ OH 1 A48 CH ₂ O Me 1 A48 OO Me 1 A49 CH ₂ OH 1 A49 OO Me 1 A50 CH ₂ OH 1 A50 OO Me 1 A51 CH ₂ OH 1 A51 OO Me 1 A52 CH ₂ OH 1 A52 OO Me 1 A53 CH ₂ OH 1 A53 OO Me 1 A54 CH 2 OH 1 A54 OO Me 1 A55 CH 2 OH 1 A55 OO Me 1 A56 CH 2 OH 1 A56 OO Me 1 A57 CH 2 OH 1 A57 OO Me 1 ---- ---------------

Table 13 shows the compound groups AA7 to ZZ7.

Table 13

[0248]

Embedded image

[0249]

[Table 13]

Table 14 shows examples of combinations of the substituents A, X, and Y in each of the compound groups AA7 to ZZ7.

[0251]

[Table 14] Table 14 ――――――――――――――――――――――――― AXY ――――――――――――――――― ―――――――― A1 NOMe H A1 NOMe Me A1 NOMe Et A1 NOMe CO ₂ Me A1 NOMe CO ₂ Et A1 NOMe CN A1 NOMe OMe A1 NOMe NH ₂ A1 NOMe NHMe A1 NOMe NMe ₂ A1 NOEt Me A2 NOMe H A2 NOMe Me A2 NOMe Et A2 NOMe CO ₂ Me A2 NOMe CN A2 NOMe OMe A2 NOMe NH ₂ A2 NOMe NHMe A2 NOMe NMe ₂ A2 NOEt Me A2 NOCH ₂ CH = CH ₂ Me A2 NOCH ₂ CH = CH ₂ Et A2 NOCH ₂ CH = CH ₂ CO ₂ Me A2 CHCN Me A2 C (CN) ₂ Me A2 CHOMe Me A2 NPh Me A3 NOMe H A3 NOMe Me A3 NOMe Et A3 NOMe CO ₂ Me A3 NOMe CO ₂ Et A3 NOMe CN A3 NOMe OMe A3 NOMe NH ₂ A3 NOMe NHMe A3 NOMe NEt ₂ A3 NOEt Me A3 NOEt CO ₂ Me A3 NOiPr Me A3 NOCH ₂ CH = CH ₂ Me A3 NOCH ₂ CH = CH ₂ Et A3 NOCH ₂ CH = CH ₂ CO ₂ Me A3 NOCH ₂ CH = CH ₂ CO ₂ nBu A3 CHCN Me A3 C (CN) ₂ Me A3 C (CN) CO ₂ Me Me A3 NPh Me A4 NOMe Me A4 NOMe Et A4 NOMe nHex A4 NOMe CO ₂ Me A4 NOMe CO ₂ Et A4 NOMe CN A4 NOMe OMe A4 NOMe NH ₂ A4 NOMe NHMe A4 NOMe NE t ₂ A4 NOnHex Me A4 NOCH ₂ CH = CH ₂ Me A4 NOCH ₂ CH = CH ₂ Et A4 NOCH ₂ CH = CH ₂ CO ₂ Me A4 NOCH ₂ CH = CH ₂ SMe A4 CHCN Me A4 C (CN) ₂ Me A4 C (CN) CO ₂ Me Me A4 NPh Me A5 NOMe Me A5 NSMe Et A5 NCN COMe A5 NOMe CO ₂ Me A6 CHCO ₂ Me CH = CH ₂ A6 NOCH = CH ₂ CF ₃ A6 NNO ₂ CH ₂ OMe A6 NNMe ₂ C (S) NHMe A7 NCH = CH ₂ OCH = CH ₂ A7 CHC≡CH OCF ₃ A7 NOCF ₃ OCH ₂ CH = CH ₂ A7 N- (1-Piperidyl) cHex A8 NOMe Me A8 NOC≡CH 1-Pyrazolyl A8 NCOPh C ≡CH A8 NOPh CO ₂ Me A9 NOMe Me A9 NCF ₃ OC≡CH A9 NOCONMe ₂ OCF = CF ₂ A10 NOMe H A10 NOMe Me A10 NOH Me A10 NOH Et A10 NOMe Et A10 NOMe iPr A10 NOMe nHex A10 NOMe CO ₂ Me A10 NOMe COMe A10 NOMe CO ₂ Et A10 NOMe CONHMe A10 NOMe CONMe ₂ A10 NOMe CN A10 NOMe OMe A10 NOMe OEt A10 NOMe SMe A10 NOMe NH ₂ A10 NOMe NHMe A10 NOMe NMe ₂ A10 NOMe NEt ₂ A10 NOMe CF ₃ A10 NOEt Me A10 NOEt _{Et A10 NOEt CO 2 Me A10 NOnPr} Me A10 NOnBu Me A10 NOnOct C (S) Me A10 NOiPr Me A10 NOCH 2 CH = CH 2 Me A10 NOCH 2 CH = CH 2 Et A10 NOCH 2 CH = CH 2 CO 2 Me A10 NOCH ₂ CH = CH ₂ CO ₂ Et A10 CHCN Me A10 C (CN) ₂ M e A10 C (CN) CO ₂ Me Me A10 CHOMe Me A10 CHNO ₂ Me A10 NPh Me A10 N- (2-Pyridyl) Me A10 NOPh Me A10 NOC (O) Me Me A10 NOC (O) tBu Me A10 NOC (O ) CF ₃ Me A10 NSMe Et A10 NCN Me A10 NOCF = CF ₂ Ph A10 NOC≡CF cPr A10 NNO ₂ Me A10 NNO ₂ S (O) Me A10 NNMe ₂ Me A10 NNMe ₂ CO ₂ Me A10 NNMe ₂ SO ₂ Me A10 NS (O) Me C (S) NMe ₂ A10 NSO ₂ Me OC≡CF A10 NcHex 3-Pyridyl A10 NCH ₂ OMe 1-Piperidyl A10 NCOMe 1-Imidazolyl A10 NCOCF ₃ 1-Pyrazolinyl A10 NCO ₂ Me 1-Morpholinyl A10 N -(1-Morpholinyl) Me A10 N- (1-Morpholinyl) CO ₂ Me A10 O Ph A10 O 3-Pyridyl A10 O 1-Piperidyl A10 O 1-Imidazolyl A10 O 1-Pyrazolinyl A10 O 1-Morpholinyl A10 S Ph A10 S 3-Pyridyl A10 S 1-Piperidyl A10 S 1-Imidazolyl A10 S 1-Pyrazolinyl A10 S 1-Morpholinyl A11 NOMe H A11 NOMe Me A11 NOMe Et A11 NOMe CO ₂ Me A11 NOMe CO ₂ Et A11 NOMe CN A11 NOMe OMe A11 NOMe NH ₂ A11 NOMe NHMe A11 NOMe NEt ₂ A11 NOEt Me A11 NOEt CO ₂ Me A11 NOiPr Me A11 NOCH ₂ CH = CH ₂ Me A11 NOCH ₂ CH = CH ₂ Et A11 NOCH ₂ CH = CH ₂ CO ₂ Me A11 NOCH ₂ CH = CH ₂ CO ₂ nBu A11 CHCN Me A11 C (CN) ₂ Me A11 C (CN) CO ₂ Me Me A11 NPh Me A12 NOMe H A12 NOMe Me A12 NOMe Et A12 NOMe CO ₂ Me A12 NOMe CN A12 NOMe OMe A12 NOMe NH ₂ A12 NOMe NHMe A12 NOMe NEt ₂ A12 NOEt Me A12 NOEt CO ₂ Me A12 NOiPr Me A12 NOCH ₂ CH = CH ₂ Me A12 NOCH ₂ CH = CH ₂ Et A12 NOCH ₂ CH = CH ₂ CO ₂ Me A12 CHCN Me A12 C (CN) ₂ Me A12 C (CN ) CO ₂ Me Me A13 NOEt Et A13 NOCH ₂ CH = CH ₂ Me A13 NOMe CO ₂ Me A14 NOEt Me A14 NOCH ₂ CH = CH ₂ Me A14 NOMe CO ₂ Me A15 NOEt Me A15 NOCH ₂ CH = CH ₂ iPr A15 NOMe CO ₂ Me A16 NOMe Me A16 NOEt Me A16 NOCH ₂ CH = CH ₂ NEt ₂ A16 NOMe CONHMe A17 NOMe Me A17 NOEt Me A17 NOCH ₂ CH = CH ₂ NEt ₂ A17 NOPh CONHMe A18 NOEt Me A18 NOCH ₂ CH = CH ₂ NEt ₂ A18 NOC (O) tBu OnBu A19 NOEt Me A19 NOCH ₂ CH = CH ₂ NnPr ₂ A19 NOMe OiPr A20 NOEt Me A20 NOCH ₂ CH = CH ₂ COnBu A20 NSnBu OtBu A21 NOEt Me A21 NOCH ₂ CH = CH ₂ CONHEt A21 NOtBu Me A22 NOMe Me A22 NOEt Me A22 NOCH ₂ CH = CH ₂ Me A22 NOMe CO ₂ Me A23 NOMe Me A23 NOEt Me A23 NOCH ₂ CH = CH ₂ Me A23 NOMe CO ₂ Me A24 NOMe H A24 NOMe Me A24 NOMe Et A24 NOMe CO ₂ Me A24 NOMe CN A24 NOMe OMe A24 NOMe NH ₂ A24 NOMe NHMe A24 NOMe NEt ₂ A24 NOEt Me A24 NOEt CO ₂ Me A24 NOiPr Me A24 NOCH ₂ CH = CH ₂ Me A24 NOCH ₂ CH = CH ₂ Et A24 NOCH ₂ CH = CH ₂ CO ₂ Me A24 CHCN Me A24 C (CN) ₂ Me A24 C (CN) CO ₂ Me Me A25 NOMe H A25 NOMe Me A25 NOMe Et A25 NOMe CO ₂ Me A25 NOMe CO ₂ Et A25 NOMe CN A25 NOMe OMe A25 NOMe NH ₂ A25 NOMe NHMe A25 NOMe NEt ₂ A25 NOEt Me A25 NOEt CO ₂ Me A25 NOiPr Me A25 NOCH ₂ CH = CH ₂ Me A25 NOCH ₂ CH = CH ₂ Et A25 NOCH ₂ CH = CH ₂ CO ₂ Me A25 NOCH ₂ CH = CH ₂ CN A25 CHCN Me A25 C (CN) ₂ Me A25 C (CN) CO ₂ Et Me A25 NPh Me A26 NOMe Me A26 NOEt Me A26 NOCH ₂ CH = CH ₂ Me A26 NOMe CO ₂ Me A27 NOEt Me A27 NOCH ₂ CH = CH ₂ Me A27 NOMe CO ₂ Me A28 NOEt Me A28 NOCH ₂ CH = CH ₂ Me A28 NOMe CO ₂ Me A29 NOEt Me A29 NOCH ₂ CH = CH ₂ Me A29 NOMe CO ₂ Me A30 NOEt Me A30 NOCH ₂ CH = _{CH 2 Me A30 nOMe CO 2 Me} A31 nOMe H A31 nOMe Me A31 nOMe Et A31 nOMe CO 2 Me A31 nOMe CN A31 nOMe OMe A31 nOMe NH 2 A31 nOMe NHMe A31 nOMe NEt 2 A31 NOEt Me A31 NOEt CO 2 Me A31 NOiPr Me A31 NOCH ₂ CH = CH ₂ Me A31 NOCH ₂ CH = CH ₂ Et A31 NOCH ₂ CH = CH ₂ CO ₂ Me A31 NOCH ₂ CH = CH ₂ CN A31 CHCN Me A31 C (CN) ₂ Me A31 C (CN) CO ₂ Et Me A32 NOMe H A32 NOMe Me A32 NOMe Et A32 NOMe CO ₂ Me A32 NOMe CO ₂ Et A32 NOMe CN A32 NOMe OMe A32 NOMe NH ₂ A32 NOMe NHMe A32 NOMe NEt ₂ A32 NOEt Me A32 NOEt CO ₂ Me A32 NOiPr Me A32 NOCH ₂ CH = CH ₂ Me A32 NOCH ₂ CH = CH ₂ Et A32 NOCH ₂ CH = CH ₂ CO ₂ Me A32 NOCH ₂ CH = CH ₂ CN A32 CHCN Me A32 C (CN) ₂ Me A32 C (CN) CO ₂ Et Me A32 NPh Me A33 NOEt Me A33 NOCH ₂ CH = CH ₂ Me A33 NOMe CO ₂ Me A34 NOEt Me A34 NOCH ₂ CH = CH ₂ Me A34 NOMe CO ₂ Me A35 NOMe Me A35 NOEt Me A35 NOCH ₂ CH = CH ₂ Me A35 NOMe CO ₂ Me A36 NOEt Me A36 NOCH ₂ CH = CH ₂ Me A36 NOMe CO ₂ Me A37 NOMe Me A37 NOEt Me A37 NOCH ₂ CH = CH ₂ Me A37 NOMe CO ₂ Me A38 NOEt Me A38 NOCH ₂ CH = CH ₂ Me A38 NOMe CO ₂ Me A39 NOEt Me A39 NOCH ₂ CH = CH ₂ Me A39 NOMe CO ₂ Me A40 NOEt Me A40 NOCH ₂ CH = CH ₂ Me A40 NOMe CO ₂ Me A41 NOMe Me A41 NOEt Me A41 NOCH ₂ CH = CH ₂ Me A41 NOMe CO ₂ Me A41 NOMe CN A42 NOEt Me A42 NOCH ₂ CH = CH ₂ Me A42 NO Me CO ₂ Me A42 NOMe CN A43 NOEt Me A43 NOCH ₂ CH = CH ₂ Me A43 NOMe CO ₂ Me A44 NOMe Me A44 NOEt Me A44 NOCH ₂ CH = CH ₂ Me A44 NOMe CO ₂ Me A44 NOMe CN A45 NOMe H A45 NOMe Me A45 NOH Me A45 NOH Et A45 nOMe Et A45 nOMe iPr A45 nOMe nHex A45 nOMe CO 2 Me A45 nOMe COMe A45 nOMe CONHMe A45 nOMe CONMe 2 A45 nOMe CN A45 nOMe OMe A45 nOMe OEt A45 nOMe SMe A45 nOMe NH 2 A45 nOMe NHMe A45 NOMe NMe ₂ A45 NOMe NEt ₂ A45 NOMe CF ₃ A45 NOEt Me A45 NOEt Et A45 NOEt CO ₂ Me A45 NOnPr Me A45 NOnBu Me A45 NOnOct C (S) Me A45 NOiPr Me A45 NOCH ₂ CH = CH ₂ Me A45 NOCH ₂ CH = CH ₂ Et A45 NOCH ₂ CH = CH ₂ CO ₂ Me A45 NOCH ₂ CH = CH ₂ CO ₂ Et A45 CHCN Me A45 C (CN) ₂ Me A45 C (CN) CO ₂ Me Me A45 CHOMe Me A45 CHNO ₂ Me A45 NPh Me A45 N- (2-Pyridyl) Me A45 NOPh Me A45 NOC (O) Me Me A45 NOC (O) tBu Me A45 NOC (O) CF ₃ Me A45 NSMe Et A45 NCN Me A45 NOCF = CF ₂ Ph A45 NOC≡CF cPr A45 NNO ₂ Me A45 NNO ₂ S (O) Me A45 NNMe ₂ Me A45 NNMe ₂ CO ₂ Me A45 NNMe ₂ SO ₂ Me A45 NS (O) Me C (S) NMe ₂ A45 NSO ₂ Me OC ≡CF A45 NcHex 3-Pyridyl A45 NOMe 1-Pi peridyl A45 NOMe 1-Imidazolyl A45 NOMe 1-Pyrazolinyl A45 NOMe 1-Morpholinyl A45 N- (1-Morpholinyl) Me A45 N- (1-Morpholinyl) CO ₂ Me A45 O Ph A45 O 3-Pyridyl A45 O 1-Piperidyl A45 O 1-Imidazolyl A45 O 1-Pyrazolinyl A45 O 1-Morpholinyl A45 S Ph A45 S 3-Pyridyl A45 S 1-Piperidyl A45 S 1-Imidazolyl A45 S 1-Pyrazolinyl A45 S 1-Morpholinyl A46 NOEt Me A46 NOCH ₂ CH = CH ₂ Me A47 NOEt Me A47 NOCH ₂ CH = CH ₂ Me A47 NOMe CO ₂ Me A48 NOEt Me A48 NOCH ₂ CH = CH ₂ Me A48 NOMe CO ₂ Me A48 NOMe CN A49 NOMe Me A49 NOEt Me A49 NOMe CO ₂ Me A50 NOEt Me A50 NOCH ₂ CH = CH ₂ Me A51 NOEt Me A51 NOCH ₂ CH = CH ₂ Me A51 NOMe CO ₂ Me A52 NOEt Me A52 NOMe CO ₂ Me A53 NOEt Me A53 NOMe CO ₂ Me A54 NOEt Me A54 NOMe CO ₂ Me A55 NOEt Me A55 NOMe CO ₂ Me A56 NOEt Me A56 NOCH ₂ CH = CH ₂ Me A56 NOMe CO ₂ Me A57 NOEt Me A57 NOMe CO ₂ Me ―――――――――――――――――― ―――――――

Table 15 shows compound groups AA8 to ZZ8.

Table 15

[0254]

Embedded image

[0255]

[Table 15]

Table 16 shows examples of combinations of the substituents A, X ² , X ³ and l in each of the compound groups AA8 to ZZ8.

[0257]

[Table 16] Table 16 ――――――――――――――――― AX ² X ³ l ――――――――――――――――― A1 CH ₂ O 1 A1 CH ₂ S 1 A1 CH ₂ NMe 1 A1 OO 1 A1 OO 2 A1 OS 1 A1 OS 2 A1 O NMe 1 A1 SO 1 A1 SS 1 A1 S NMe 1 A1 NMe O 1 A1 NMe S 1 A1 NMe NMe 3 A2 CH ₂ O 1 A2 CH ₂ S 1 A2 CH ₂ NMe 1 A2 OO 1 A2 OO 2 A2 OS 1 A2 OS 2 A2 O NMe 1 A2 SO 1 A2 SS 1 A2 S NMe 1 A2 NEt O 1 A2 NMe S 1 A3 CH ₂ O 1 A3 CH ₂ S1 A3 CH ₂ NMe 1 A3 OO 1 A3 OO 2 A3 OS 1 A3 OS 2 A3 O NMe 1 A3 SO 1 A3 SS 1 A3 S NMe 1 A3 NPh O 1 A3 NMe S 1 A4 CH ₂ O 1 A4 CH ₂ S 1 A4 CH ₂ NMe 1 A4 OO 1 A4 OO 2 A4 OS 1 A4 OS 2 A4 O NMe 1 A4 SO 1 A4 SS 1 A4 S NMe 1 A4 NEt O 1 A4 NCO ₂ Me S 1 A5 CH ₂ S 1 A5 OS 2 A6 CH ₂ S 1 A6 OS 2 A7 CH ₂ S 1 A7 OS 2 A8 CH ₂ S 1 A8 OS 2 A9 CH ₂ S 1 A9 OO 2 A9 OS 2 A10 CH ₂ CH ₂ 1 A10 CH ₂ O 1 A10 CH ₂ S 1 A10 CH ₂ NMe 1 A10 O CH ₂ 1 A10 OO 1 A10 OO 2 A10 OS 1 A10 OS 2 A10 O NMe 1 A10 O NMe 2 A10 S CH ₂ 1 A10 SO 1 A10 SS 1 A10 S NMe 1 A10 NMe CH ₂ 1 A10 NMe O 1 A10 NH ₂ O 2 A10 NMe S 1 A10 NMe NMe 2 A11 CH ₂ O 1 A11 CH ₂ S 1 A11 CH ₂ NMe 1 A11 OO 1 A11 OO 2 A11 OS 1 A11 OS 2 A11 O NMe 1 A11 SO 1 A11 SS 1 A11 S NC (O) Ph 1 A11 NcPr O 1 A11 NC (O) Me S 1 A12 CH ₂ S 1 A12 OS 2 A13 CH ₂ S 1 A13 OS 2 A14 CH ₂ S 1 A14 OS 2 A15 CH ₂ S 1 A15 OS 2 A16 CH ₂ S 1 A16 OO 2 A16 OS 2 A17 CH ₂ S 1 A17 OO 2 A17 OS 2 A18 CH ₂ S 1 A18 OS 2 A19 CH ₂ S 1 A19 OO 2 A19 OS 2 A20 CH ₂ S 1 A20 OS 2 A21 CH ₂ S 1 A21 OS 2 A22 CH ₂ S 1 A22 OO 2 A22 OS 2 A23 CH ₂ S 1 A23 OO 2 A23 OS 2 A24 CH ₂ O 1 A24 CH ₂ S1 A24 CH ₂ NMe 1 A24 OO 1 A24 OO 2 A24 OS 1 A24 OS 2 A24 O NMe 1 A24 SO 1 A24 SS 1 A24 S NnHex 1 A24 NcPr O 1 A24 NMe S 1 A25 CH ₂ O 1 A25 CH ₂ S1 A25 CH ₂ NMe 1 A25 OO 1 A25 OO 2 A25 OS 1 A25 OS 2 A25 O NMe 1 A25 SO 1 A25 SS 1 A25 S NnHex 1 A25 NcPr O 1 A25 NMe S 1 A26 CH ₂ S 1 A26 OO 2 A26 OS 2 A27 CH ₂ S 1 A27 OS 2 A28 CH ₂ S 1 A28 OS 2 A29 CH ₂ S 1 A29 OS 2 A30 CH ₂ S 1 A30 OS 2 A31 CH ₂ O 1 A31 CH ₂ S 1 A31 CH ₂ NMe 1 A31 OO 1 A31 OO 2 A31 OS 1 A31 OS 2 A31 O NMe 1 A31 SO 1 A31 SS 1 A31 S NMe 1 A31 NMe O 1 A31 NMe S 1 A32 CH ₂ O 1 A32 CH ₂ S 1 A32 CH ₂ NMe 1 A32 OO 1 A32 OO 2 A32 OS 1 A32 OS 2 A32 O NMe 1 A32 SO 1 A32 SS 1 A32 S NMe 1 A32 NMe O 1 A32 NMe S 1 A33 CH ₂ S 1 A33 OS 2 A34 CH ₂ S 1 A34 OS 2 A35 CH ₂ S 1 A35 OS 2 A36 CH ₂ S 1 A36 OS 2 A37 CH ₂ S 1 A37 OO 2 A37 OS 2 A38 CH ₂ S 1 A38 OS 2 A39 CH ₂ S 1 A39 OS 2 A40 CH ₂ S 1 A40 OS 2 A41 CH ₂ S 1 A41 OS 2 A42 CH ₂ S 1 A42 OS 2 A43 CH ₂ S 1 A43 OS 2 A44 CH ₂ S 1 A44 OS 2 A45 CH ₂ O 1 A45 CH ₂ S 1 A45 CH ₂ NMe 1 A45 OO 1 A45 OO 2 A45 OS 1 A45 OS 2 A45 O NMe 1 A45 SO 1 A45 SS 1 A45 S NMe 1 A45 NMe O 1 A45 NMe S 1 A46 CH ₂ S 1 A46 OS 2 A47 CH ₂ S 1 A47 OS 2 A48 CH ₂ S 1 A48 OS 2 A49 CH ₂ S 1 A49 OS 2 A50 CH ₂ S 1 A50 OS 2 A51 CH ₂ S 1 A51 OS 2 A52 CH ₂ S 1 A52 OS 2 A53 CH ₂ S 1 A53 OS 2 A54 CH ₂ S 1 A54 OS 2 A55 CH ₂ S 1 A55 OS 2 A56 CH ₂ S 1 A56 OS 2 A57 CH ₂ S 1 A57 OS 2 ―――――――――――――――――

The compound groups AA9 to ZZ9 are shown in Table 17.

Table 17

[0260]

Embedded image

[0261]

[Table 17]

Table 18 shows examples of combinations of the substituents A, X ² , X ³ , R ³ , and l in each of the compound groups AA9 to ZZ9.

[0263]

[Table 18] Table 18 ―――――――――――――――――――― AX ² X ³ R ³ l ―――――――――――――――― ―――― A1 CH ₂ OH 1 A1 CH ₂ O Me 1 A1 CH ₂ OH 2 A1 CH ₂ O Me 2 A1 CH ₂ O nHex 1 A1 CH ₂ SH 1 A1 CH ₂ S Me 1 A1 CH ₂ S Me 2 A1 CH ₂ NMe H 1 A1 CH ₂ NMe Me 1 A1 CH ₂ NMe Me 2 A1 OOH 1 A1 OO Me 1 A1 OOH 2 A1 OO Me 2 A1 OSH 1 A1 OS Me 2 A1 O NCO ₂ Me H 1 A1 O NMe Me 1 A1 O NMe Me 2 A1 SSH 1 A1 SS Me 1 A1 SS Me 2 A1 S NC (O) Me H 1 A1 S NMe Me 1 A1 S NPh Me 2 A1 NMe NMe H 1 A1 NMe NMe Me 1 A1 NMe NcPr Me 2 A2 CH ₂ OH 1 A2 CH ₂ O Me 1 A2 CH ₂ OH 2 A2 CH ₂ O Me 2 A2 CH ₂ SH 1 A2 CH ₂ S Me 1 A2 CH ₂ S Me 2 A2 CH ₂ NMe H 1 A2 CH ₂ NMe Me 1 A2 CH ₂ NMe Me 2 A2 OOH 1 A2 OO Me 1 A2 OOH 2 A2 OO Me 2 A2 OSH 1 A2 OS Me 2 A2 O NMe H 1 A2 O NMe Me 1 A2 O NMe Me 2 A2 SSH 1 A2 SS Me 1 A2 SS Me 2 A2 S NCH ₂ OMe H 1 A2 S NMe Me 1 A2 S NMe Me 2 A2 NMe NMe H 1 A2 NMe NMe Me 1 A2 NMe NMe Me 2 A3 CH ₂ OH 1 A3 CH ₂ O Me 1 A3 CH ₂ OH 2 A3 CH ₂ O Me 2 A3 CH ₂ SH 1 A3 CH ₂ S Me 1 A3 CH ₂ S Me 2 A3 CH ₂ NMe H 1 A3 CH ₂ NMe Me 1 A3 CH ₂ NMe Me 2 A3 OOH 1 A3 OO Me 1 A3 OOH 2 A3 OO Me 2 A3 OSH 1 A3 OS Me 2 A3 O NMe H 1 A3 O NMe Me 1 A3 O NMe Me 2 A3 SSH 1 A3 SS Me 1 A3 SS Me 2 A3 S NC (O) Ph H 1 A3 S NMe Me 1 A3 S NCH ₂ Ph Me 2 A3 NMe NCH = CH ₂ H 1 A3 NMe NMe Me 1 A3 NMe NC≡CH Me 2 A4 CH ₂ OH 1 A4 CH ₂ O Me 1 A4 CH ₂ OH 2 A4 CH ₂ O Me 2 A4 CH ₂ SH 1 A4 CH ₂ S Me 1 A4 CH ₂ S Me 2 A4 CH ₂ NMe H 1 A4 CH ₂ NMe Me 1 A4 CH ₂ NMe Me 2 A4 OOH 1 A4 OO Me 1 A4 OOH 2 A4 OO Me 2 A4 OSH 1 A4 OS Me 2 A4 O NMe Me 1 A4 SSH 1 A4 SS Me 1 A4 SS Me 2 A4 S NMe Me 1 A4 NMe NMe Me 1 A5 CH ₂ OH 1 A5 OO Me 1 A6 CH ₂ OH 1 A6 OO Me 1 A7 CH ₂ OH 1 A7 OO Me 1 A8 CH ₂ OH 1 A8 OO Me 1 A9 CH ₂ OH 1 A9 OO Me 1 A10 CH ₂ OH 0 A10 CH ₂ OH 1 A10 CH ₂ O Me 0 A10 CH ₂ O Me 1 A10 CH ₂ OH 2 A10 CH ₂ OH 3 A10 CH ₂ O Me 2 A10 CH ₂ O Et 1 A10 CH ₂ SH 1 A10 CH ₂ SH 2 A10 CH ₂ S Me 1 A10 CH ₂ S Me 2 A10 CH ₂ NH H 1 A10 CH ₂ NMe H 1 A10 CH ₂ NMe H 2 A10 CH ₂ NMe Me 1 A10 CH ₂ NMe Me 2 A10 OOH 1 A10 OO Me 1 A10 OOH 2 A10 OOH 3 A10 OO Me 2 A10 OSH 1 A10 OSH 2 A10 OS Me 1 A10 OS Me 2 A10 O NHH 1 A10 O NMe H 1 A10 O NMe H 2 A10 O NMe Me 1 A10 O NMe Me 2 A10 SSH 1 A10 SSH 2 A10 SS Me 1 A10 SS Me 2 A10 S NHH 1 A10 S NMe H 1 A10 S NMe H 2 A10 S NMe Me 1 A10 S NMe Me 2 A10 NMe NH H 1 A10 NMe NMe H 1 A10 NMe NMe H 2 A10 NMe NMe Me 1 A10 NMe NMe Me 2 A11 CH ₂ OH 1 A11 CH ₂ O Me 1 A11 CH ₂ OH 2 A11 CH ₂ O Me 2 A11 CH ₂ SH 1 A11 CH ₂ S Me 1 A11 CH ₂ S Me 2 A11 CH ₂ NMe H 1 A11 CH ₂ NMe Me 1 A11 CH ₂ NMe Me 2 A11 OOH 1 A11 OO Me 1 A11 OOH 2 A11 OO Me 2 A11 OSH 1 A11 OS Me 2 A11 O NMe Me 1 A11 SSH 1 A11 SS Me 1 A11 SS Me 2 A11 S NMe Me 1 A11 NMe NMe Me 1 A12 CH ₂ OH 1 A12 CH ₂ O Me 1 A12 OO Me 1 A13 CH ₂ OH 1 A13 OO Me 1 A14 CH ₂ OH 1 A14 OO Me 1 A15 CH ₂ OH 1 A15 CH ₂ OH Me 1 A16 CH ₂ OH 1 A16 CH ₂ O Me 1 A16 OO Me 1 A17 CH ₂ OH 1 A17 CH ₂ O Me 1 A17 OO Me 1 A18 CH ₂ OH 1 A18 OO Me 1 A19 CH ₂ OH 1 A19 CH ₂ O Me 1 A19 OO Me 1 A20 CH ₂ OH 1 A20 OO Me 1 A21 CH ₂ OH 1 A21 OO Me 1 A22 CH ₂ OH 1 A22 CH ₂ O Me 1 A22 OO Me 1 A23 CH ₂ OH 1 A23 CH ₂ O Me 1 A23 OO Me 1 A24 CH ₂ OH 1 A24 CH ₂ O Me 1 A24 CH ₂ OH 2 A24 CH ₂ O Me 2 A24 CH ₂ SH 1 A24 CH ₂ SMe 1 A24 CH ₂ NMe H 1 A24 CH ₂ NMe Me 1 A24 OOH 1 A24 OO Me 1 A24 OOH 2 A24 OO Me 2 A24 SS Me 1 A24 SS Me 2 A24 NMe NMe Me 1 A25 CH ₂ OH 1 A25 CH ₂ O Me 1 A25 CH ₂ OH 2 A25 CH ₂ O Me 2 A25 CH ₂ SH 1 A25 CH ₂ S Me 1 A25 CH ₂ NMe H 1 A25 CH ₂ NMe Me 1 A25 OOH 1 A25 OO Me 1 A25 OOH 2 A25 OO Me 2 A25 SS Me 1 A25 SS Me 2 A25 NMe NMe Me 1 A26 CH ₂ OH 1 A26 CH ₂ O Me 1 A26 OO Me 1 A27 CH ₂ OH 1 A27 OO Me 1 A28 CH ₂ OH 1 A28 OO Me 1 A29 CH ₂ OH 1 A29 OO Me 1 A30 CH ₂ OH 1 A30 OO Me 1 A31 CH ₂ OH 1 A31 CH ₂ O Me 1 A31 CH ₂ OH 2 A31 CH ₂ O Me 2 A31 CH ₂ SH 1 A31 CH ₂ S Me 1 A31 CH ₂ NMe H 1 A31 CH ₂ NMe Me 1 A31 OOH 1 A31 OO Me 1 A31 OOH 2 A31 OO Me 2 A31 SS Me 1 A31 SS Me 2 A31 NMe NMe Me 1 A32 CH ₂ OH 1 A32 CH ₂ O Me 1 A32 CH ₂ OH 2 A32 CH ₂ O Me 2 A32 CH ₂ SH 1 A32 CH ₂ S Me 1 A32 CH ₂ NMe H 1 A32 CH ₂ NMe Me 1 A32 OOH 1 A32 OO Me 1 A32 O OH 2 A32 OO Me 2 A32 SS Me 1 A32 SS Me 2 A32 NMe NMe Me 1 A33 CH ₂ OH 1 A33 OO Me 1 A34 CH ₂ OH 1 A34 OO Me 1 A35 CH ₂ OH 1 A35 CH ₂ O Me 1 A35 OO Me 1 A36 CH ₂ OH 1 A36 OO Me 1 A37 CH ₂ OH 1 A37 CH ₂ O Me 1 A37 OO Me 1 A38 CH ₂ OH 1 A38 OO Me 1 A39 CH ₂ OH 1 A39 OO Me 1 A40 CH ₂ OH 1 A40 OO Me 1 A41 CH ₂ OH 1 A41 CH ₂ O Me 1 A41 OO Me 1 A42 CH ₂ OH 1 A42 OO Me 1 A43 CH ₂ OH 1 A43 OO Me 1 A44 CH ₂ OH 1 A44 OO Me 1 A45 CH ₂ OH 1 A45 CH ₂ O Me 1 A45 CH ₂ OH 2 A45 CH ₂ O Me 2 A45 CH ₂ SH 1 A45 CH ₂ S Me 1 A45 CH ₂ NMe H 1 A45 CH ₂ NMe Me 1 A45 OOH 1 A45 OO Me 1 A45 OOH 2 A45 OO Me 2 A45 SS Me 1 A45 SS Me 2 A45 NMe NMe Me 1 A46 CH ₂ OH 1 A46 OO Me 1 A47 CH ₂ OH 1 A47 OO Me 1 A48 CH ₂ OH 1 A48 OO Me 1 A49 CH ₂ OH 1 A49 OO Me 1 A50 CH ₂ OH 1 A50 OO Me 1 A51 CH ₂ OH 1 A51 OO Me 1 A52 CH ₂ OH 1 A52 OO Me 1 A53 CH ₂ OH 1 A53 OO Me 1 A54 CH ₂ OH 1 A54 OO Me 1 A55 CH ₂ OH 1 A55 OO Me 1 A56 CH ₂ OH 1 A56 OO Me 1 A57 CH ₂ OH 1 A57 OO Me 1 ――――――――――――――――――――

The compound groups AA10 to ZZ10 are shown in Table 19.

Table 19

[0266]

Embedded image

[0267]

[Table 19]

Table 20 shows examples of combinations of the substituents A, X, and Y in each of the compound groups AA10 to ZZ10.

[0269]

[Table 20] Table 20 ――――――――――――――――――――――――― AXY ――――――――――――――――― ―――――――― A1 NOMe Me A1 NOMe Et A1 NOMe CO ₂ Me A1 NOMe CN A1 NOMe OMe A1 NOMe NH ₂ A1 NOMe NHMe A1 NOMe NMe ₂ A1 NOEt Me A2 NOMe Me A2 NOMe Et A2 NOMe CO ₂ Me A2 nOMe CN A2 nOMe OMe A2 nOMe NH 2 A2 nOMe NHMe A2 nOMe NMe 2 A2 NOEt Me A2 NOCH 2 CH = CH 2 Me A2 NOCH 2 CH = CH 2 Et A2 NOCH 2 CH = CH 2 CO 2 Me A2 CHCN Me A2 C (CN) ₂ Me A3 NOMe Me A3 NOMe Et A3 NOMe CO ₂ Me A3 NOMe CN A3 NOMe OMe A3 NOMe NH ₂ A3 NOMe NHMe A3 NOMe NEt ₂ A3 NOEt Me A3 NOEt CO ₂ Me A3 NOiPr Me A3 NOCH ₂ CH = CH ₂ Me A3 NOCH ₂ CH = CH ₂ Et A3 NOCH ₂ CH = CH ₂ CO ₂ Me A3 NOCH ₂ CH = CH ₂ CO ₂ nBu A3 CHCN Me A3 C (CN) ₂ Me A3 C (CN) CO ₂ Me Me A4 NOMe Me A4 NOMe nHex A4 NOMe CO ₂ Me A4 NOMe CN A4 NOMe OMe A4 NOMe NH ₂ A4 NOMe NHMe A4 NOMe NEt ₂ A4 NOnHex Me A4 NOCH ₂ CH = CH ₂ Me A4 NOCH ₂ CH = CH ₂ Et A4 NOCH ₂ CH = CH ₂ CO ₂ Me A4 NOCH ₂ CH = CH ₂ SMe A4 CHCN Me A4 C (CN) ₂ Me A4 C (CN) CO ₂ Me Me A5 NOMe Me A5 NSMe Et A5 NCN COMe A5 NOMe CO ₂ Me A6 CHCO ₂ Me CH = CH ₂ A6 NOCH = CH ₂ CF ₃ A6 NNO ₂ CH ₂ OMe A6 NNMe ₂ C (S) NHMe A7 NCH = CH ₂ OCH = CH ₂ A7 CHC≡CH OCF ₃ A7 NOCF ₃ OCH ₂ CH = CH ₂ A7 N- (1-Piperidyl) cHex A8 NOMe Me A8 NOC≡CH 1- Pyrazolyl A8 NCOPh C≡CH A8 NOPh CO ₂ Me A9 NOMe Me A9 NCF ₃ OC≡CH A9 NOCONMe ₂ OCF = CF ₂ A10 NOMe H A10 NOMe Me A10 NOH Me A10 NOH Et A10 NOMe Et A10 NOMe iPr A10 NOMe nHex A10 NOMe CO ₂ Me A10 NOMe COMe A10 NOMe CO ₂ Et A10 NOMe CONHMe A10 NOMe CONMe ₂ A10 NOMe CN A10 NOMe OMe A10 NOMe OEt A10 NOMe SMe A10 NOMe NH ₂ A10 NOMe NHMe A10 NOMe NMe ₂ A10 NOMe NEt ₂ A10 NOMe CF ₃ A10 NOEt Me A10 NOEt Et A10 NOEt CO ₂ Me A10 NOnPr Me A10 NOnBu Me A10 NOnOct C (S) Me A10 NOiPr Me A10 NOCH ₂ CH = CH ₂ Me A10 NOCH ₂ CH = CH ₂ Et A10 NOCH ₂ CH = CH ₂ CO ₂ Me A10 NOCH ₂ CH = CH ₂ CO ₂ Et A10 CHCN Me A10 C (CN) ₂ Me A10 C (CN) CO ₂ Me Me A10 CHOMe Me A10 CHNO ₂ Me A10 NPh Me A10 N- (2-Pyridyl) Me A10 NOPh Me A10 NOC (O) Me Me A10 NOC (O) tBu Me A10 N OC (O) CF ₃ Me A10 NSMe Et A10 NCN Me A10 NOCF = CF ₂ Ph A10 NOC≡CF cPr A10 NNO ₂ Me A10 NNO ₂ S (O) Me A10 NNMe ₂ Me A10 NNMe ₂ CO ₂ Me A10 NNMe ₂ SO ₂ Me A10 NS (O) Me C (S) NMe ₂ A10 NSO ₂ Me OC≡CF A10 NcHex 3-Pyridyl A10 NCH ₂ OMe 1-Piperidyl A10 NCOMe 1-Imidazolyl A10 NCOCF ₃ 1-Pyrazolinyl A10 NCO ₂ Me 1- Morpholinyl A10 N- (1-Morpholinyl) Me A10 N- (1-Morpholinyl) CO ₂ Me A10 O Ph A10 O 3-Pyridyl A10 O 1-Piperidyl A10 O 1-Imidazolyl A10 O 1-Pyrazolinyl A10 O 1-Morpholinyl A10 S Ph A10 S 3-Pyridyl A10 S 1-Piperidyl A10 S 1-Imidazolyl A10 S 1-Pyrazolinyl A10 S 1-Morpholinyl A11 NOMe Me A11 NOMe Et A11 NOMe CO ₂ Me A11 NOMe CN A11 NOMe OMe A11 NOMe NH ₂ A11 NOMe NHMe A11 NOMe NEt ₂ A11 NOEt Me A11 NOEt CO ₂ Me A11 NOiPr Me A11 NOCH ₂ CH = CH ₂ Me A11 NOCH ₂ CH = CH ₂ Et A11 NOCH ₂ CH = CH ₂ CO ₂ Me A11 CHCN Me A11 C (CN) ₂ Me A11 C (CN) CO ₂ Me Me A12 NOMe Me A12 NOMe Et A12 NOMe CO ₂ Me A12 NOMe CN A12 NOMe OMe A12 NOMe NH ₂ A12 NOMe NHMe A12 NOEt Me A12 NOEt CO ₂ Me A12 NOCH ₂ CH = CH ₂ Me A12 NOCH ₂ CH = CH ₂ Et A12 NOCH ₂ CH = CH ₂ CO ₂ Me A12 CHCN Me A12 C (CN) ₂ Me A12 C (CN) CO ₂ Me Me A13 NOEt Et A13 NOCH ₂ CH = CH ₂ Me A14 NOEt Me A14 NOCH ₂ CH = CH ₂ Me A15 NOEt Me A15 NOCH ₂ CH = CH ₂ iPr A16 NOEt Me A16 NOMe CONHMe A17 NOEt Me A17 NOCH ₂ CH = CH ₂ NEt ₂ A18 NOEt Me A18 NOCH ₂ CH = CH ₂ NEt ₂ A19 NOEt Me A19 NOCH ₂ CH = CH ₂ NnPr ₂ A20 NOEt Me A20 NOCH ₂ CH = CH ₂ COnBu A21 NOEt Me A21 NOCH ₂ CH = CH ₂ CONHEt A22 NOEt Me A22 NOCH ₂ CH = CH ₂ Me A22 NOMe CO ₂ Me A23 NOEt Me A23 NOCH ₂ CH = CH ₂ Me A23 NOMe CO ₂ Me A24 NOMe Me A24 NOMe Et A24 NOMe CO ₂ Me A24 NOMe CN A24 NOMe OMe A24 NOMe NH ₂ A24 NOMe NHMe A24 NOEt Me A24 NOEt CO ₂ Me A24 NOiPr Me A24 NOCH ₂ CH = CH ₂ Me A24 NOCH ₂ CH = CH ₂ Et A24 NOCH ₂ CH = CH ₂ CO ₂ Me A24 CHCN Me A24 C (CN) ₂ Me A24 C (CN) CO ₂ Me Me A25 NOMe Me A25 NOMe Et A25 NOMe CO ₂ Me A25 NOMe CN A25 NOMe OMe A25 NOMe NH ₂ A25 NOMe NHMe A25 NOMe NEt ₂ A25 NOEt Me A25 NOEt CO ₂ Me A25 NOiPr Me A25 NOCH ₂ CH = CH ₂ Me A25 NOCH ₂ CH = CH ₂ Et A25 NOCH ₂ CH = CH ₂ CO ₂ Me A25 NOCH ₂ CH = CH ₂ CN A25 CHCN Me A25 C (CN) ₂ Me A25 C (CN) CO ₂ Et Me A26 NOMe Me A26 NOCH ₂ CH = CH ₂ Me A26 NOMe CO ₂ Me A27 NOEt Me A27 NOMe CO ₂ Me A28 NOEt Me A28 NOCH ₂ CH = CH ₂ Me A29 NOEt Me A29 NOCH ₂ CH = CH ₂ Me A30 NOCH ₂ CH = CH ₂ Me A30 NOMe CO ₂ Me A31 NOMe Me A31 NOMe Et A31 NOMe CO ₂ Me A31 NOMe CN A31 NOMe OMe A31 NOMe NH ₂ A31 NOMe NHMe A31 NOMe NEt ₂ A31 NOEt Me A31 NOiPr Me A31 NOCH ₂ CH = CH ₂ Me A31 NOCH ₂ CH = CH ₂ Et A31 NOCH ₂ CH = CH ₂ CO ₂ Me A31 NOCH ₂ CH = CH ₂ CN A31 CHCN Me A31 C (CN) ₂ Me A31 C (CN) CO ₂ Et Me A32 NOMe Me A32 NOMe Et A32 NOMe CO ₂ Me A32 NOMe CN A32 NOMe OMe A32 NOMe NH ₂ A32 NOMe NHMe A32 NOMe NEt ₂ A32 NOEt Me A32 NOEt CO ₂ Me A32 NOiPr Me A32 NOCH ₂ CH = CH ₂ Me A32 NOCH ₂ CH = CH ₂ Et A32 NOCH ₂ CH = CH ₂ CO ₂ Me A32 NOCH ₂ CH = CH ₂ CN A32 CHCN Me A32 C (CN) ₂ Me A32 C (CN) CO ₂ Et Me A33 NOEt Me A33 NOCH ₂ CH = CH ₂ Me A34 NOEt Me A34 NOCH ₂ CH = CH ₂ Me A35 NOEt Me A35 NOCH ₂ CH = CH ₂ Me A36 NOEt Me A36 NOCH ₂ CH = CH ₂ Me A37 NOCH ₂ CH = CH ₂ Me A37 NOMe CO ₂ Me A38 NOEt Me A38 NOCH ₂ CH = CH ₂ Me A39 NOEt Me A39 NOCH ₂ CH = CH ₂ Me A40 NOEt Me A40 NOCH ₂ CH = CH ₂ Me A41 NOEt Me A41 NOCH ₂ CH = CH ₂ Me A41 NOMe CO ₂ Me A41 NOMe CN A42 NOEt Me A42 NOCH ₂ CH = CH ₂ Me A42 NOMe CN A43 NOCH ₂ CH = CH ₂ Me A43 NOMe CO ₂ Me A44 NOEt Me A44 NOCH ₂ CH = CH ₂ Me A44 NOMe CN A45 NOMe Me A45 NOH Me A45 NOH Et A45 NOMe Et A45 NOMe nHex A45 NOMe CO ₂ Me A45 NOMe COMe A45 NOMe CO ₂ Et A45 NOMe CONHMe A45 NOMe CN A45 NOMe OMe A45 NOMe OEt A45 NOMe SMe A45 NOMe NH ₂ A45 NOMe NHMe A45 NOMe NMe ₂ A45 NOMe NEt ₂ A45 NOEt Me A45 NOEt Et A45 NOEt CO ₂ Me A45 NOnBu Me A45 NOiPr Me A45 NOCH ₂ CH = CH ₂ Me A45 NOCH ₂ CH = CH ₂ Et A45 NOCH ₂ CH = CH ₂ CO ₂ Me A45 CHCN Me A45 C (CN) ₂ Me A45 C (CN) CO ₂ Me Me A45 CHOMe Me A45 CHNO ₂ Me A45 NOPh Me A45 NOC (O) Me Me A45 NOC (O) tBu Me A45 NCN Me A45 NNMe ₂ Me A45 NS (O) Me C (S) NMe ₂ A45 NSO ₂ Me OC≡CF A45 NOMe 1-Piperidyl A45 NOMe 1-Imidazolyl A45 NOMe 1-Pyrazolinyl A45 NOMe 1-Morpholinyl A45 N- (1-Morpholinyl) Me A45 N- (1-Morpholinyl) CO ₂ Me A45 O 1 -Piperidyl A45 O 1-Imidazolyl A45 O 1-Pyrazolinyl A45 O 1-Morpholinyl A45 S 1-Imidazolyl A45 S 1-Pyrazolinyl A45 S 1-Morpholinyl A46 NOEt Me A46 NOCH ₂ CH = CH ₂ Me A47 NOCH ₂ CH = CH ₂ Me A47 NOMe CO ₂ Me A48 NOEt Me A48 NOCH ₂ CH = CH ₂ Me A49 NOCH ₂ CH = CH ₂ Me A49 NOMe CO ₂ Me A50 NOEt Me A50 NOCH ₂ CH = CH ₂ Me A51 NOEt Me A51 NOCH ₂ CH = CH ₂ Me A52 NOEt Me A52 NOCH ₂ CH = CH ₂ Me A53 NOEt Me A53 NOCH ₂ CH = CH ₂ Me A54 NOEt Me A54 NOCH ₂ CH = CH ₂ Me A55 NOEt Me A55 NOCH ₂ CH = CH ₂ Me A56 NOEt Me A56 NOCH ₂ CH = CH ₂ Me A57 NOEt Me A57 NOCH ₂ CH = CH ₂ Me ―――――――――――――――――――――――――

The compound groups AA11 to ZZ11 are shown in Table 21.

Table 21

[0272]

Embedded image

[0273]

[Table 21]

Table 22 shows examples of combinations of the substituents A, X and 1 in each of the compound groups AA11 to ZZ11.

[0275]

[Table 22] Table 22 ――――――――――――――――――― AX l ――――――――――――――――――― A1 NOMe 1 A1 NOMe 2 A1 NOMe 3 A1 NOEt 2 A2 NOMe 1 A2 NOMe 2 A2 NOMe 3 A2 NOEt 2 A2 NOCH ₂ CH = CH ₂ 1 A2 NOCH ₂ CH = CH ₂ 2 A2 NOCH ₂ CH = CH ₂ 3 A2 CHCN 2 A2 C (CN) ₂ 2 A2 CHOMe 2 A2 NPh 2 A3 NOMe 1 A3 NOMe 2 A3 NOMe 3 A3 NOEt 2 A3 NOiPr 2 A3 NOCH ₂ CH = CH ₂ 1 A3 NOCH ₂ CH = CH ₂ 2 A3 NOCH ₂ CH = CH ₂ 3 A3 CHCN 2 A3 C (CN) ₂ 2 A3 C (CN) CO ₂ Me 2 A3 NPh 2 A4 NOMe 1 A4 NOMe 2 A4 NOMe 3 A4 NOnHex 2 A4 NOCH ₂ CH = CH ₂ 1 A4 NOCH ₂ CH = CH ₂ 2 A4 NOCH ₂ CH = CH ₂ 3 A4 CHCN 2 A4 C (CN) ₂ 2 A4 C (CN) CO ₂ Me 2 A4 NPh 2 A5 NOMe 2 A5 NSMe 2 A5 NCN 2 A6 CHCO ₂ Me 2 A6 NOCH = CH ₂ 2 A6 NNO ₂ 2 A6 NNMe ₂ 2 A7 NCH = CH ₂ 2 A7 CHC≡CH 2 A7 NOCF ₃ 2 A7 N- (1-Piperidyl) 2 A8 NOMe 2 A8 NOC≡CH 2 A8 NCOPh 2 A8 NOPh 2 A9 NOMe 2 A9 NCF ₃ 2 A9 NOCONMe ₂ 2 A10 NOMe 1 A10 NOMe 2 A10 NOH 1 A10 NOH 2 A10 NOMe 3 A10 NOEt 2 A10 NOnPr 2 A10 NOnBu 2 A10 NOnOct 2 A10 NOiPr 2 A10 NOCH ₂ CH = CH ₂ 1 A10 NOCH ₂ CH = CH ₂ 2 A10 CHCN 2 A10 C (CN) ₂ 2 A10 C (CN) CO ₂ Me 2 A10 CHOMe 2 A10 CHNO ₂ 2 A10 NPh 2 A10 N- (2-Pyridyl) 2 A10 NOPh 2 A10 NOC (O) Me 2 A10 NOC (O) tBu 2 A10 NOC (O) CF ₃ 2 A10 NSMe 2 A10 NCN 2 A10 NOCF = CF ₂ 2 A10 NOC≡CF 2 A10 NNO ₂ 2 A10 NNMe ₂ 2 A10 NS ( O) Me 2 A10 NSO ₂ Me 2 A10 NcHex 2 A10 NCH ₂ OMe 2 A10 NCOMe 2 A10 NCOCF ₃ 2 A10 NCO ₂ Me 2 A10 N- (1-Morpholinyl) 2 A10 N- (1-Morpholinyl) 2 A10 O 1 A10 O 2 A10 O 3 A10 S 1 A10 S 2 A10 S 3 A11 NOMe 1 A11 NOMe 2 A11 NOMe 3 A11 NOEt 2 A11 NOiPr 2 A11 NOCH ₂ CH = CH ₂ 1 A11 NOCH ₂ CH = CH ₂ 2 A11 NOCH ₂ CH = CH ₂ 3 A11 CHCN 2 A11 C (CN) ₂ 2 A11 C (CN) CO ₂ Me 2 A11 NPh 2 A12 NOMe 1 A12 NOMe 2 A12 NOMe 3 A12 NOEt 2 A12 NOiPr 2 A12 NOCH ₂ CH = CH ₂ 1 A12 NOCH ₂ CH = CH ₂ 2 A12 NOCH ₂ CH = CH ₂ 3 A12 CHCN 2 A12 C (CN) ₂ 2 A12 C (CN) CO ₂ Me 2 A13 NOEt 2 A13 NOCH ₂ CH = CH ₂ 2 A14 NOEt 2 A14 NOCH ₂ CH = CH ₂ 2 A15 NOEt 2 A15 NOCH ₂ CH = CH ₂ 2 A16 NOEt 2 A16 NOCH ₂ CH = CH ₂ 2 A17 NOEt 2 A17 NOCH ₂ CH = CH ₂ 2 A18 NOEt 2 A18 NOCH ₂ CH = CH ₂ 2 A19 NOEt 2 A19 NOCH ₂ CH = CH ₂ 2 A20 NOEt 2 A20 NOCH ₂ CH = CH ₂ 2 A21 NOEt 2 A21 NOCH ₂ CH = CH ₂ 2 A22 NOEt 2 A22 NOCH ₂ CH = CH ₂ 2 A23 NOEt 2 A23 NOCH ₂ CH = CH ₂ 2 A24 NOMe 1 A24 NOMe 2 A24 NOEt 2 A24 NOiPr 2 A24 NOCH ₂ CH = CH ₂ 1 A24 NOCH ₂ CH = CH ₂ 2 A24 CHCN 2 A24 C (CN) ₂ 2 A24 C (CN) CO ₂ Me 2 A25 NOMe 1 A25 NOMe 2 A25 NOMe 3 A25 NOEt 2 A25 NOiPr 2 A25 NOCH ₂ CH = CH ₂ 1 A25 NOCH ₂ CH = CH ₂ 2 A25 CHCN 2 A25 C (CN) ₂ 2 A25 C (CN) CO ₂ Et 2 A26 NOMe 2 A26 NOEt 2 A26 NOCH ₂ CH = CH ₂ 2 A27 NOEt 2 A27 NOCH ₂ CH = CH ₂ 2 A28 NOEt 2 A28 NOCH ₂ CH = CH ₂ 2 A29 NOEt 2 A29 NOCH ₂ CH = CH ₂ 2 A30 NOEt 2 A30 NOCH ₂ CH = CH ₂ 2 A31 NOMe 1 A31 NOMe 2 A31 NOEt 2 A31 NOiPr 2 A31 NOCH ₂ CH = CH ₂ 1 A31 NOCH ₂ CH = CH ₂ 2 A31 CHCN 2 A31 C (CN) ₂ 2 A31 C (CN) CO ₂ Et 2 A32 NOMe 1 A32 NOMe 2 A32 NOMe 3 A32 NOEt 2 A32 NOiPr 2 A32 NOCH ₂ CH = CH ₂ 1 A32 NOCH ₂ CH = CH ₂ 2 A32 CHCN 2 A32 C (CN) ₂ 2 A32 C (CN) CO ₂ Et 2 A33 NOEt 2 A33 NOCH ₂ CH = CH ₂ 2 A34 NOEt 2 A34 NOCH ₂ CH = CH ₂ 2 A35 NOEt 2 A35 NOCH ₂ CH = CH ₂ 2 A36 NOEt 2 A36 NOCH ₂ CH = CH ₂ 2 A37 NOEt 2 A37 NOCH ₂ CH = CH ₂ 2 A38 NOEt 2 A38 NOCH ₂ CH = CH ₂ 2 A39 NOEt 2 A39 NOCH ₂ CH = CH ₂ 2 A40 NOEt 2 A40 NOCH ₂ CH = CH ₂ 2 A41 NOEt 2 A41 NOCH ₂ CH = CH ₂ 2 A42 NOEt 2 A42 NOCH ₂ CH = CH ₂ 2 A43 NOEt 2 A43 NOCH ₂ CH = CH ₂ 2 A44 NOEt 2 A44 NOCH ₂ CH = CH ₂ 2 A45 NOMe 1 A45 NOMe 2 A45 NOH 1 A45 NOH 2 A45 NOMe 3 A45 NOEt 2 A45 NOnOct 2 A45 NOiPr 2 A45 NOCH ₂ CH = CH ₂ 1 A45 NOCH ₂ CH = CH ₂ 2 A45 CHCN 2 A45 C (CN) ₂ 2 A45 C (CN) CO ₂ Me 2 A45 CHOMe 2 A45 CHNO ₂ 2 A45 NOPh 2 A45 NOC (O) Me 2 A45 NOC (O) tBu 2 A45 NOC (O) CF 2 A45 NCN 2 A45 NNO ₂ 2A45 O 1 A45 O 2 A45 O 3 A45 S 1 A45 S 2 A45 S 3 A46 NOEt 2 A46 NOCH ₂ CH = CH ₂ 2 A47 NOEt 2 A47 NOCH ₂ CH = CH ₂ 2 A48 NOEt 2 A48 NOCH ₂ CH = CH ₂ 2 A49 NOEt 2 A49 NOCH ₂ CH = CH ₂ 2 A50 NOEt 2 A50 NOCH ₂ CH = CH ₂ A51 NOEt 2 A51 NOCH ₂ CH = CH ₂ 2 A52 NOEt 2 A52 NOCH ₂ CH = CH ₂ 2 A53 NOEt 2 A53 NOCH ₂ CH = CH ₂ 2 A54 NOEt 2 A54 NOCH ₂ CH = CH ₂ 2 A55 NOEt _{2 A55 NOCH 2 CH = CH 2} 2 A56 NOEt 2 A56 NOCH 2 CH = CH 2 2 A57 NOEt 2 A57 NOCH 2 CH = CH 2 2 --------------- ---

When the compound of the present invention is applied as a pesticidal agent, it is usually mixed with a suitable solid carrier or liquid carrier, and if necessary, a surfactant, a penetrant, a spreading agent, a thickener, a deicing agent, Binders, anti-caking agents, disintegrating agents and decomposition inhibitors, etc., are added, and liquids, emulsions, wettable powders, aqueous solvents,
It can be put to practical use in any form of formulation such as water dispersible granules, aqueous solvents for granules, suspensions, emulsions, suspoemulsions, microemulsions, powders, granules and gels. Further, from the viewpoint of labor saving and improvement of safety, the above-mentioned preparation of any dosage form can be provided by being enclosed in a water-soluble package.

Examples of 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 styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene fatty acid ester. Nonionic surfactants such as oxyethylene sorbitan fatty acid 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, if necessary, when formulating or spraying. It may be applied in combination with an agent, synergist, fertilizer, soil conditioner and the like.

[0283] In particular, by mixing and applying other pesticides or plant hormones, it is expected that the cost can be reduced by reducing the amount of applied medicine, the insecticidal spectrum can be expanded by the synergistic action of the mixed drug, and a higher pest control effect can be expected. On this occasion,
A combination with a plurality of known pesticides is also possible at the same time. Examples of the kind of agrochemical used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm
Chemicals Handbook), 1994, and the like. Specific examples of the common names are as follows, but are not necessarily limited thereto.

Fungicide: acibenzola
r), ampropylfos, anilazine (a
nilazine), azaconazole, azoxystrobin, benalaxil
xyl), benodanil, benomyl
l), benzamacril, binapacryl, biphenyl, biertanol, bitoxanol, bethoxazine,
Bordeaux mixture, blasticidin-
S (blasticidin-S), bromoconazol
e), bupirimate, butiobate (but
hiobate), calcium polysulfide (calcium polys)
ulfide), captafol, captan, copper oxychlo
ride), carpropamid, carbendazim, carbendin, carboxin, quinomethionate, clobenthiazon (chlobenthiazone), chlorfenazole
zol), chloroneb, chlorothalonil (ch
lorothalonil), chlozolinate, kufraneb,

Cymoxanil, cyproconazol, cyprodinil (cyprodini)
l), cyprofuram (cyprofuram), debacarb (debac
arb), dichlorophen, diclobutrazol, diclofuranide (diclhlo)
fluanid), diclomedine, dichloran, dietofencar
b), diclosymet, difenoconazole, diflumetorin
im), dimethirimol,

Dimethomorph, diniconazole, diniconazole-M (dinicon
azole-M), dinocap, diphenylamine, dipyrithione,
Ditalimphos (ditalimfos), dithianon (dithiano)
n), dodemorph, dodine, dorazoxolon, edefenophos (edifen)
phos), epoxyconazole (epoxiconazole), etaconazole (etaconazole), etirimol (ethirimo)
l), etridiazole, famoxadone, fenarimol, febuconazole, fenfuram
am),

Fenpiclonil, fenpropidin, fenpropimorph (f
enpropimorph), fentin, ferbam, ferimzone, fluazinam, fludioxonil,
Fluorimide, fluquinconazole, flusilazol
e), Flusulfamide, Flutolanil, Flutriafol (flutriafo)
l), folpet, fosetyl-aluminum, fuberidazole
azole), furalaxyl, fenamidone, fenhexamid,

Guazatine, hexachlorobenzene, hexaconazole (h
exaconazole), hymexazol, imazalil, imibenconazole
le), iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane (isoprot)
hiolane), iprovalicarb,

Kasugamycin, kresoxim-methyl, mankappa (m
ancopper), mancozeb (mancozeb), manneb (mane
b), mepanipyrim (mepanipyrim), mepronil (mepr
onil), metalaxyl, metconazole, metiram, metominostrobin, microbutanyl (myclobu)
tanil), nabam, nickel bis (dimethyldithiocarbamate)
mate), nitrothal-isopropyl
ropyl), nuarimol, octillinone (oct)
hilinone), ofurace, oxadixyl, oxycarboxin,
Oxpoconazole fumarat
e),

Pefurzoate, penconazole, pencicuron
n), phthalide, piperaline (piperali)
n), polyoxins (polyoxins), probenazole (pr
obenazole), prochloraz, procymidone, propamocarb hydrochloride
carbhydrochloride), propiconazo
le), propineb, pyrazophos
os), pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozen
e),

Sulfur, spiroxamine (spirox)
amine), tebuconazole, tecnazene, tetraconazol
e), thiabendazole, thifluzamide, thiophanate-methyl (thioph
anate-methyl), thiram, tolclofos-methyl, tolylfluide
anid),

[0294] Triadimefon, triadimenol, triazoxide
xide), tricyclazole, tridemorph, triflumizol
e), triforine, triticonazole (tr
iticonazole, validamycin, vinclozolin, zineb and ziram.

Bactericide: Streptomycin (st
reptomycin, oxyterracycline
ine) and oxolinic acid.

A nematicide: aldoxycarb (aldoxycar)
b), fosthiazate, fosthietan, oxamyl, fenamiphos and the like.

Acaricides: amitraz, bromopropylate, chinomethionat, chlorobenzilate
late), clofentezine, cyhexatine, dicofol, dienochlor, etoxaz
ole), fenazaquin, fenbutatin oxide, fenpropathrin, fenproxim
ate), halfenprox, hexythiazox, milbemectin (milbe)
mectin), propargite, pyridaben, pyrimidifen and tebufenpyrad.

Insecticides: abamectin, acephate, acetamipir
id), azinphos-methyl, bendiocarb, benfurac
arb), bensultap, bifenthrin, buprofezin, butocarboxin, carbary
l), Carbofuran, Carbosulfan, Cartap, Cartol, Chlorfenapyr, Chlorpyrifos
os), chlorfenvinphos, chlorfluazuron, chlorthianidin, chromafenozid
e), chlorpyrifos-methyl,
Cyfluthrin, beta-cyfluthrin, cypermethrin
n), cyromazine,

Cyhalothrin, lambda
Cyhalothrin (lambda-cyhalothrin), deltamethrin (deltamethrin), diafenthiuron (diafenthiuro)
n), diazinon, diacloden (diacl)
oden), diflubenzuron, dimethylvinphos, diphenolane (dio)
fenolan), disulfoton, dimethoate, EPN, esfenvalerate (esf)
envalerate), ethiofencarb,
Ethiprole, etofenprox (e
tofenprox), etrimfos, fenitrothion, fenobucar
b), fenoxycarb (fenoxycarb), fenpropathrin (fenpropathrin), fenvalerate (fenvale)
rate), fipronil, flucythrinate, flufenoxulone
ron), flufenprox, tau-
Tau-fluvalinate, honophos (fonop)
hos), formetanate, formothion, furathiocar
b),

Halofenozide, hexaflumuron, hydramethylnon (hydr)
amethylnon), imidacloprid, isofenphos, indoxacarb (indo
xacarb), isoprocarb, isoxathion, lufenuron,
Malathion, metaldehyd
e), methamidophos, methidathion, methacrifos, metalcarb, metalcarb, methomil, methoprene, methoxychlor
hlor), methoxyfenozide, monocrotophos, muscaule
lure), nitenpyram, omethoate, oxydemeton-methyl
methyl), oxamyl,

Parathion, Parathion-
Methyl (parathion-methyl), permethrin (permethr)
in), phenthoate, phoxime (ph
oxim), phorate, phosalon
e), phosmet, phosphamidon (phosph
amidon), pirimicarb, pirimiphos-
Methyl (pirimiphos-methyl), profenophos (profe
nofos), pymetrozine, pyraclofos, pyriproxyfe
n), rotenone, sulprofo
s), silafluofen, spinosad, sulfotep, tebfenozide, teflubenzur
on), tefluthorin, terbufos (ter
bufos), tetrachlorovinpho
s), thiodicarb, thiomethoxam (t
hiamethoxam), thiofanox, thiometon, tolfenpyra
d), tralomethrin, trichlorfon, triazuron, triflumuron, and vamidot
hion).

The applied amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops and the like, but is generally 0.000 per hectare (ha) as an active ingredient.
About 5 to 50 kg is appropriate.

Next, specific examples of the formulation of the preparation when the compound of the present invention is used will be shown. However, the composition examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others, 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 and decomposition inhibitors. 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 granule] Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, a binder and a decomposition inhibitor. 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, formulation examples of the preparation will be shown more specifically.

[Formulation Example 1] Water-dispersible compound of the present compound No. 1 17 20 parts Pyrophyllite 76 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] Milk Compound of the present compound No. 1 175 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) 17 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C 0.5 parts (Anionic surfactant: Toho Chemical Industry Corporation trade name) 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) 17 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: Shionogi Pharmaceutical Co., Ltd.) After uniformly mixing and pulverizing the above, adding a small amount of water, stirring and mixing, granulating with an extruder, drying and granulating water. It should be a Japanese medicine.

[Formulation Example 5] Granules Compound of the present invention No. 5 175 parts bentonite 50 parts talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed by stirring, granulated by an extrusion granulator, and dried to obtain granules.

[Formulation Example 6] Powder Compound No. 173 parts Carplex # 80D 0.5 parts (Synthetic hydrated silica: trade name of Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to obtain a powder.

For use, the above water-dispersible powder, emulsion, flowable powder and water-dispersible granule are diluted 50 to 20,000 times with water and sprayed, and other formulations are sprayed directly.

When the compound of the present invention is used as an anti-biofouling agent in water, the anti-fouling agent in water can be applied to a wide range of subjects by formulating it in an appropriate dosage form such as a paint, a solution, an emulsion, pellets or flakes. It can be used by appropriately selecting a commonly used technique such as application, spraying, impregnation, addition in water, installation in water, and the like according to the place of use, purpose, and dosage form. For the preparation of these paints, solutions, emulsions and the like, commonly used recipes can be adopted. Further, for example, the compound of the present invention is incorporated at the production stage of a rope or a fiber material used for a fishing net or the like, and the rope or the fiber material itself is used in a dosage form and a method other than those described above, such as imparting an underwater biofouling control property. You can do it. The underwater anti-fouling agent of the present invention may be used alone, or may be used as a mixture with an under-water anti-fouling agent other than the present invention.

When the underwater biofouling inhibitor of the present invention is used in the form of an antifouling paint, for example, the compound of the present invention is blended with a film-forming agent to prepare the paint before use. As the coating film forming agent, oil varnish, synthetic resin, artificial rubber and the like are used. Further, a solvent, a pigment or the like may be used as needed. When the paint is prepared, the concentration of the compound of the present invention has no upper limit as long as a coating film can be formed.
It is blended at a ratio of 20% by weight.

When the underwater biofouling inhibitor of the present invention is used in the form of a solution, for example, a solution prepared by dissolving the compound of the present invention in a solvent together with a film-forming agent is used. As the coating film forming agent, synthetic resin, artificial rubber, natural resin and the like are used, and as the solvent, xylene, toluene, cumene,
Methyl ethyl ketone, methyl isobutyl ketone, acetone and the like are used. Further, if necessary, an additive such as a plasticizer may be used. When preparing a solution, the compound of the present invention has no upper limit in concentration as long as a solution can be formed, but is compounded at a ratio of 1 to 50% by weight, preferably 5 to 30% by weight based on the weight of the solution. .

When the underwater anti-biofouling agent of the present invention is used in the form of an emulsion, a surfactant is usually added to the compound of the present invention to prepare a desired emulsion according to a general method for preparing an emulsion. The type of surfactant used is not particularly limited. When the emulsion is prepared, the compound of the present invention has no upper limit in the concentration as long as the emulsion can be formed, but is blended at a ratio of 1 to 50% by weight, preferably 5 to 30% by weight based on the weight of the emulsion. .

When the underwater biofouling inhibitor of the present invention is used in the form of pellets or flakes, the compound of the present invention and, if necessary, a hydrophilic resin such as polyethylene glycol which is solid at ordinary temperature are used as a base. A plasticizer, a surfactant, and the like may be blended as constituent components, and pelletized or flaked by a method such as melt molding or compression molding and used. When the pellets or flakes are prepared, the concentration of the compound of the present invention has no upper limit as long as the pellets or flakes can be formed, but it is 20 to 95% by weight, preferably 30 to 9% by weight based on the weight of the pellets or flakes.
It is blended at a ratio of 0% by weight.

[0322]

[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] (Compound 8) 2- [3- (2-aza-2-methoxy-1)
-Methylvinyl) pyrazolyl] -2-cyano-1-
Synthesis of (1,3,4-trimethylpyrazol-5-yl) vinyl-2,2-dimethylpropanoate.

[0324]

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1) Synthesis of 3-acetylpyrazole To 10 g of 3,3-dimethoxy-2-butanone was added under ice-cooling
Tertiary butoxybis (dimethylamino) methane 1
5.8 g were added dropwise. After stirring at room temperature for 18 hours, the orange liquid obtained by shrinking was diluted with 50 ml of methanol,
Under ice cooling, 4 g of hydrazine monohydrate was added dropwise, and the mixture was heated under reflux for 3 hours. After evaporating the solvent, the mixture was diluted with 50 ml of acetone, 0.5 ml of water and 0.5 g of p-toluenesulfonic acid were added, and the mixture was heated under reflux for 3 hours. After evaporating the solvent, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1) to obtain 5.14 g of the desired product.

2) Synthesis of 1-aza-1-methoxy-2-pyrazol-3-ylprop-1-ene 4.84 g of 3-acetylpyrazole was added to 70 ml of ethanol.
And, under ice-cooling, 5.41 g of sodium acetate and 4.41 g of methoxyamine hydrochloride were successively added. After stirring at room temperature for 18 hours, the solvent was distilled off, the residue was dissolved in 50 ml of water, and extracted with 50 ml of ethyl acetate. The organic layer was successively washed with 50 ml of water and 30 ml of saturated saline, dried over sodium sulfate, and the solvent was distilled off to obtain 6.02 g of the desired product.

3) Synthesis of 2- [3- (2-aza-2-methoxy-1-methylvinyl) pyrazolyl] ethanenitrile 6.02 g of the compound obtained in 2) was dissolved in 44 ml of a 1N aqueous potassium hydroxide solution. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure. The obtained salt was suspended in 50 ml of tetrahydrofuran, and 3.33 g of chloroacetonitrile was added dropwise thereto under ice cooling. After stirring at room temperature for 18 hours, the reaction solution was added to 100 ml of water.
And extracted twice with 100 ml of ethyl acetate. The organic layer was successively washed with 50 ml of water and 50 ml of saturated saline, and then dried over sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (chloroform) to obtain 3.06 g of the desired product.

4) (Compound 9) 2- [3- (2-aza-
2-methoxy-1-methylvinyl) pyrazolyl] -3-
Synthesis of hydroxy-3- (1,3,4-trimethylpyrazol-5-yl) prop-2-ennitrile 0.71 g and 0.82 g of the compound obtained in 3) were dissolved in 20 ml of tetrahydrofuran, and the solution was cooled under ice-cooling. 0.99 g of potassium tert-butoxide was added. After stirring at room temperature for 2 hours, the solvent was distilled off, and the residue was dissolved in 30 ml of water and washed with 20 ml of hexane. The aqueous layer was made acidic with an aqueous hydrochloric acid solution and extracted with 50 ml of ethyl acetate. The organic layer was washed with 30 ml of saturated saline and dried over sodium sulfate, and then the solvent was distilled off to obtain 0.83 g of the desired product. Melting point: 111-113 ° C. 5) 0.7 g of the compound obtained in 4) was added to tetrahydrofuran 2
Then, 0.27 g of triethylamine was added thereto, and 0.27 g of pivaloyl chloride was further added under ice-cooling. After stirring at room temperature for 18 hours, the solvent was distilled off, suspended in 30 ml of water, and extracted with 30 ml of ethyl acetate. The organic layer was washed with 20 ml of saturated saline and dried over sodium sulfate.
The solvent was distilled off. The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 0.86 g of the target compound (compound 8).

1H-NMR (CDCl3, δ ppm); 1.19 (9H, s), 2.13 (3
H, s), 2.22 (3H, s), 2.26 (3H, s), 3.90 (3H, s), 3.99 (3H,
s), 6.79 (1H, s), 7.65 (1H, s) [Synthesis Example 2] (Compound 18) 2- [3- (2-aza-1-methyl-2)
-Prop-2-enyloxyvinyl) pyrazolyl] -3
Synthesis of -hydroxy-3- (1,3,4-trimethylpyrazol-5-yl) prop-2-ennitrile.

[0330]

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2- (3-acetylpyrazolyl) -2-cyano-1- (1,3,4-trimethylpyrazole-5
Il) vinyl-2,2-dimethylpropanoate 0.9
8 g were dissolved in 20 ml of ethanol, to which 0.45 g of allyloxyamine hydrochloride and 0.7 g of sodium acetate were successively added. After stirring at room temperature for 18 hours, the solvent was distilled off.
After suspending in 30 ml of water, the mixture was extracted with 30 ml of ethyl acetate. The organic layer was washed with 20 ml of a saturated saline solution, dried over sodium sulfate, and then the solvent was distilled off.
1.05 g was obtained.

1H-NMR (CDCl3, δ ppm); 2.13 (3H, s), 2.21 (3
H, s), 2.29 (3H, s), 3.90 (3H, s), 4.70 (2H, m), 5.30 (2H, d
d), 6.05 (1H, m), 6.79 (1H, s), 7.65 (1H, s), 8.20 (1H, bro
ad-s) [Synthesis Example 3] (Compound 77) 2- [2- (2-aza-2-methoxy-
1-methylvinyl) (1,3-thiazol-4-yl)]
Synthesis of -2-cyano-1- (1,3,4-trimethylpyrazol-5-yl) vinyl-2,2-dimethylpropanoate.

[0333]

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1) Methyl-3-aza-3-methoxy-2
Synthesis of -methylprop-2-enoate 25.0 g of pyruvate methyl ester was added to methanol 20
The solution was dissolved in 0 ml, and 22.1 g of sodium acetate was added under ice cooling. Thereafter, 21.5 g of methoxyamine hydrochloride was slowly added in several portions, and the mixture was stirred at room temperature overnight. After filtering the inorganic substance, the solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with chloroform. The organic layer was washed with aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 22.0 g of the desired product.

2) Synthesis of 3-aza-3-methoxy-2-methylprop-2-enamide 22.0 g of the compound obtained in 1) was added to tetrahydrofuran 10
After dissolving in 0 ml, 28% aqueous ammonia 12.2 g under ice-cooling
Was added dropwise. After stirring at room temperature overnight, the solvent was distilled off under reduced pressure. The precipitated crystals were washed with hexane to obtain 15.1 g of the desired product.

3) Synthesis of 1-amino-3-aza-3-methoxy-2-methylprop-2-en-1-thione 10.0 g of the compound obtained in 2) was dissolved in 100 ml of dioxane, and then dissolved under ice-cooling. 15.3 g of Lawson's reagent was added. After stirring at room temperature for 4 hours and at 80 ° C. for 2 hours, the solvent was distilled off under reduced pressure.
After adding water and extracting with chloroform, the organic layer was successively washed with a 1N aqueous solution of sodium hydroxide and water, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2.5 g of the desired product.
I got

4) Synthesis of 1-aza-2- [4- (chloromethyl) (1,3-thiazol-2-yl)]-1-methoxyprop-1-ene 2.5 g of the compound obtained in 3) was obtained. After dissolving in 50 ml of ethanol, 2.2 g of 1,3-dichloroacetone was added at room temperature. After raising the temperature and reacting under reflux conditions for 4 hours, the solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with chloroform. The organic layer was washed with aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) and recrystallized from hexane to obtain 0.6 g of the desired product.

5) Synthesis of 2- [2- (2-aza-2-methoxy-1-methylvinyl) -1,3-thiazol-4-yl] ethanenitrile 0.14 g of sodium cyanide was dissolved in 50 ml of DMF. Under ice cooling, 0.5 g of the compound obtained in 4) was added thereto, followed by stirring at room temperature for 2 hours. After adding water, extract with chloroform,
The organic layer was washed with aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.4 g of the desired product.

6) (Compound 76) 2- [2- (2-aza-2-methoxy-1-methylvinyl) (1,3-thiazol-4-yl)]-3-hydroxy-3- (1, 3,
Synthesis of 4-trimethylpyrazol-5-yl) prop-2-ennitrile. 0.68 g of potassium tert-butoxide in THF 30 m
A suspension of 0.47 g of the compound obtained in 5) and 0.36 g of 1,3,4-trimethylpyrazole-5-carbonyl chloride in 20 ml of tetrahydrofuran was added dropwise to the suspension under ice-cooling. . After stirring at room temperature for 1 hour,
The solvent was distilled off under reduced pressure, dissolved in water and washed with diethyl ether. The aqueous layer was acidified with a 1N aqueous hydrochloric acid solution, extracted with chloroform, and dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, recrystallization from diisopropyl ether gave 0.6 g of the desired product. Melting point: 121.5-125.2 ° C 7) 0.6 g of the compound obtained in 6) was added to 50 ml of dichloromethane.
, And 0.24 g of triethylamine was added thereto.
Under ice cooling, 0.29 g of pivaloyl chloride was added. After stirring at room temperature for 2 hours, aqueous sodium bicarbonate was added, extracted with chloroform, and dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, a silica gel TLC plate (hexane: ethyl acetate =
2: 1) to give 0.32 g of the desired product (compound 77).

1H-NMR (CDCl3, δ ppm); 1.26 (9H, s), 2.10 (3
H, s), 2.21 (3H, s), 2.34 (3H, s), 3.91 (3H, s), 4.05 (3H,
s), 7.60 (1H, s) [Synthesis Example 4] (Compounds 80 and 81) methyl-2- {2- [2- (2,
2-dimethylpropanoyloxy) -1-cyano-2-
(1,3,4-trimethylpyrazol-5-yl) vinyl] (1,3-thiazol-4-yl)}-3-aza-
Synthesis of 3-methoxyprop-2-enoate.

[0341]

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1) Synthesis of methyl-3-aza-2- (2-bromoacetyl) -3-methoxyprop-2-enoate 3.0 g of methyl-2-acetyl-3-aza-3-methoxyprop-2-enoate was obtained. While dissolved in 20 ml of methanol, 3.6 g of bromine was added dropwise at room temperature, and the mixture was stirred overnight. After evaporating the solvent under reduced pressure, the residue was neutralized with an aqueous potassium carbonate solution and extracted with diethyl ether. The organic layer was washed with water and saturated saline, dried over sodium sulfate, and the solvent was distilled off to obtain 4.2 g of the desired product.

2) Methyl-3-aza-2- [2- (cyanomethyl) (1,3-thiazol-4-yl)]-3-
Synthesis of methoxyprop-2-enoate 1.76 g of cyanothioacetamide was added to 30 ml of methanol.
And 1.0 g of sodium methoxide was added. Under ice cooling, 4.2 g of the compound synthesized in 1) was added, and the mixture was stirred at room temperature for 3 hours. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and saturated saline, and dried over sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1) to obtain 2.6 g of the desired product.

3) (Compound 82) Methyl-2- {2-
[1-cyano-2-hydroxy-2- (1,3,4-trimethylpyrazol-5-yl) vinyl] (1,3-thiazol-4-yl)}-3-aza-3-methoxyprop-2- Synthesis of enoate 0.5 g of the compound obtained in 2) was dissolved in 10 ml of benzene.
0.32 g of triethylamine and a catalytic amount of N, N-dimethylaminopyridine are added. Under ice-cooling, 0.36 g of 1,3,4-trimethylpyrazole-5-carbonyl chloride was added, and the mixture was stirred at room temperature overnight. The reaction solution was poured into water, extracted with ethyl acetate, washed with water and saturated saline, and dried over sodium sulfate. After evaporating the solvent, the crystals were washed with hexane to obtain 0.6 g of the desired product. Melting point: 161 ° -164 ° C. 4) 0.5 g of the compound obtained in 3) was dissolved in 10 ml of chloroform, 0.2 g of triethylamine was added, and 0.19 g of pivaloyl chloride was added under ice-cooling. Stirred overnight. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and saturated saline, and dried over sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to isolate the desired isomer of the acrylonitrile portion.

EorZ form (Compound 81: 0.15 g)
Melting point: 161 ° -162 ° C. The above isomer (compound 80: 0.2 g) 1H-NMR (CDCl
3, δppm); 1.34 (9H, s), 1.93 (3H, s), 2.22 (3H, s), 3.64 (3
H, s), 3.93 (3H, s), 4.02 (3H, s), 7.69 (1H, s) The structures and melting points of the compounds of the present invention synthesized according to the above scheme or Examples are shown in Tables 16 to 22. Although shown, unless otherwise specified, it is a mixture of E-form and Z-form. The abbreviations in the table have the following meanings.

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

[0347]

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Table 23

[0349]

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[0350]

[Table 23] ――――――――――――――――――――――――――――――――――― No. ABXYR ¹ R ² Melting point (℃) ― ―――――――――――――――――――――――――――――――― 1 A1 'COtBu NOMe Me HH 117-119 2 A1' COtBu NOEt Me HH 84-85 3 A1 'H NOEt Me HH 95-96 4 A1' COtBu NOiPr Me HH 92-93 5 A2 'COtBu NOMe Me HH Resin 6 A2' H NOMe Me HH Resin 7 A3 'COtBu NOMe Me HH resin 8 A4 'COtBu NOMe Me HH resin 9 A4' H NOMe Me HH 111-113 10 A5 'COtBu NOMe Me HH resin 11 A5' H NOMe Me HH 105-107 12 A1 'COtBu NOnBu Me HH resin 13 A1 'COtBu N-morpholinyl Me HH resin 14 A3' H NNMe ₂ HHH resin 15 A4 'COtBu NOEt Me HH resin 16 A4' H NOEt Me HH resin 17 A4 'COtBu NOCH ₂ CH = CH ₂ Me HH resin 18 A4 'H NOCH ₂ CH = CH ₂ Me HH Resin 19 A6' COtBu NOMe Me HH 120-121 20 A4 'COtBu NOMe Me Cl H Resin 21 A6' COtBu NOMe Me Cl H 93-95, EorZ 22 A6 '' H NOMe Me Cl H 94−96 23 A5 ′ COtBu NOMe Me Cl H 97−99, EorZ 24 A5 ′ H NOMeMe Cl H 116−119 25 A4 ′ COtBu NOMe CO ₂ Me HH Resin 26 A4 ′ H NOMe CO ₂ Me HH 109− 110 27 A2 'H NOMe CO ₂ Me HH 127-128 28 A2' COtBu NOMe CO ₂ Me HH Resin, EorZ 29 A2 'COtBu NOMe CO ₂ Me HH Resin, E / Z mixture 30 A5' COtBu NOMe CO ₂ Me HH Resin 31 A5 'H NOMe CO ₂ Me HH 174-175 32 A5' COtBu NOEt CO ₂ Me H Me Resin 33 A5 'H NOEt CO ₂ Me HH 123-124 34 A5' H NOEt CO ₂ Me H Me 159−160 35 A4 'COtBu NOMe CONHMe HH Resin, EorZ 36 A4' COtBu NOMe CONMe ₂ HH Resin 37 A4 'H NOMe CONHMe HH Resin 38 A4' COtBu NOEt CO ₂ Me H H Resin 39 A6 'COtBu NOMe CO ₂ Me HH Resin 40 A6' Me NOMe CO ₂ Me HH 134-135, EorZ 41 A6 'H NOMe CO ₂ Me HH 98-100 42 A4' Me NOEt Me HH Resin 43 A4 'CH ₂ OMe NOEt Me HH resinous 44 A7' H NOMe Me Cl H 100-101 45 A7 'COtBu NOMe Me Cl H 89-90 46 A8' H NOMe Me Cl H 107-110 47 A8 'COtBu NOMe Me Cl H resin 48 A9 'H NOMe Me Cl H 75-77 49 A9' COtBu NOMe Me Cl H resin 50 A5 'CH ₂ OMe NOMe Me Cl H 92-93 51 A4' COtBu NOMe Et HH resin 52 A4 ' Me NOMe Et HH 71-72, EorZ 53 A10 'H NOMe Me HH 122-125 54 A11' COtBu NOEt Me HH 102-108 55 A11 'COtBu NOMe CO ₂ Me HH 139-140, EorZ 56 A12' H NOMe Me Cl H 161-163 57 A12 'COtBu NOMe Me Cl H 93-94 58 A4' H NOMe iPr HH Resin 59 A4 'COtBu NOMe iPr HH Resin 60 A4' H NOMe Me Me H 128-130 61 A4 'COtBu NOMe Me Me H 118-119, EorZ 62A4 'COtBu NOCOtBu Me HH Resin, EorZ 63A5' H NOEt Me Cl H 104-105 64 A5 'COtBu NOEt Me Cl H Resin 65 A5' H NOCH ₂ CH = CH ₂ Me Me H 97−99 66 A5 'COtBu NOCH ₂ CH = CH ₂ Me Me H 58-59, ZorE 67 A5 'COtBu NOCH ₂ CH = CH ₂ Me Me H resin, EorZ 68 A13' H NOCH ₂ CH = CH ₂ Me Me H 107-108 69 A13 'COtBu NOCH ₂ CH = CH ₂ Me Me H resin 70 A4' COtBu NOMe CN HH resin 71 A4 'H NOMe CN HH 131-133 72 A4' H NOH Me HH resin 73 A4 'COtBu NOPh Me HH resin 74 A4 'COtBu NOMe CO ₂ Me Me H resin, EorZ 75 A4' COtBu NOMe CO ₂ Me Me H resin, ZorE 76 A14 'COtBu NOEt Me HH resin ――――――――――― ――――――――――――――――――――――――

Table 24

[0352]

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[0353]

[Table 24] ――――――――――――――――――――――――――――――――――――― No. ABXYR ¹ R ² Melting point (℃) ― ―――――――――――――――――――――――――――――――――― 77 A3 'COtBu NOMe Me Me H 96-97 78 A3' H NOMe Me Me H 131-155 ―――――――――――――――――――――――――――――――――――

Table 25

[0355]

Embedded image

[0356]

[Table 25] ――――――――――――――――――――――――――――――――――― No. ABXYR ¹ Melting point (℃) ――― ―――――――――――――――――――――――――――――――― 79 A4 'H NOMe Me H 121.5-125.2 80 A4' COtBu NOMe Me H Resin Form, EorZ 81 A4 'COtBu NOMe CO ₂ Me H Resin, EorZ 82 A4' H NOMe CO ₂ Me H 163-164 ―――――――――――――――――――― ―――――――――――――――

Table 26

[0358]

Embedded image

[0359]

[Table 26] ――――――――――――――――――――――――――――――――――――― No. ABXYR ¹ Melting point (℃) ――― ―――――――――――――――――――――――――――――――― 83 A4 'H NOMe Me H 203-204 84 A4' COtBu NOMe Me H resin 85 A4 'COtBu NOMe CO ₂ Me H Resin, EorZ 86 A4' COtBu NOMe CO ₂ Me H 161-162, ZorE 87 A4 'H NOMe CO ₂ Me H 161-164 ―――――――― ―――――――――――――――――――――――――――――

Table 27

[0361]

Embedded image

[0362]

[Table 27] ――――――――――――――――――――――――――――――――――― No. ABXYR ¹ Melting point (℃) ――― ―――――――――――――――――――――――――――――――― 88 A4 'H NOMe Me Me 116-118 89 A4' COtBu NOMe Me Me Resin , EorZ 90 A4 'COtBu NOMe Me Me Resin, ZorE ―――――――――――――――――――――――――――――――― ―

Table 28

[0364]

Embedded image

[0365]

[Table 28] ――――――――――――――――――――――――――――――――――― No. ABX ² X ³ R ³ Melting point (℃ ) ――――――――――――――――――――――――――――――――――― 91 A4 'COtBu CH ₂ OH Resin, EorZ 92 A4 '' COtBu OO Me Resin ―――――――――――――――――――――――――――――――――

Table 29

[0367]

Embedded image

[0368]

[Table 29] ――――――――――――――――――――――――――――――――――― No. ABX Melting point (℃) ―――― ――――――――――――――――――――――――――――――― 93 A4 'H NOMe 150-153 94 A4' COtBu NOMe 125-126, EorZ ―――――――――――――――――――――――――――――――――――

Table 30

[0370]

Embedded image

[0371]

[Table 30] ――――――――――――――――――――――――――――――――――――――― No. ABXYR ¹ Melting point (℃) ――― ―――――――――――――――――――――――――――――――― 95 A5 'H NOEt CO ₂ Me Me 116-118 96 A4' COtBu NOMe CO ₂ Me H resin ―――――――――――――――――――――――――――――――――――

[Test Examples] 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 [0373] A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to give a concentration of 500 ppm. Was prepared.

This chemical 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 brown planthopper was placed in a pot for 1
0 insects were released, covered, and stored in a constant temperature room. The survey was conducted after 6 days, and the mortality was calculated from the following formula. The test was performed in two sections.

[0375]

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

Compound No. of the present invention: 1, 2, 4, 8, 1
9, 21, 49, 51, 59, 62, 69, 80

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

Compound No. of the present invention: 2, 3, 4, 5, 6,
7, 8, 9, 10, 15, 16, 17, 18, 19, 2,
0, 22, 25, 26, 27, 28, 31, 38, 3
9, 41, 43, 51, 54, 57, 58, 59, 6
0, 62, 72, 80, 96

Test Example 3 Insecticidal test against peach aphid Moist filter paper was spread on a glass petri dish having an inner diameter of 3 cm, and cabbage leaves having the same diameter were placed thereon. Four 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, adult and larval mortality was determined from the following formula. The test was performed in two sections.

[0380]

## EQU2 ## Insect rate (%) = [number of dead insects / (number of dead insects + number of surviving insects)] × 100 As a result, the following compounds showed a mortality of 80%.

Compound No. of the present invention: 1, 2, 3, 4, 5,
6, 7, 8, 9, 10, 11, 12, 13, 14, 1
5, 16, 17, 18, 19, 20, 21, 22, 2,
3, 24, 25, 26, 27, 28, 29, 30, 3,
1, 32, 33, 35, 36, 37, 38, 39, 4
0, 41, 42, 43, 44, 45, 46, 47, 4
8, 49, 50, 51, 52, 53, 54, 55, 5
6, 57, 58, 59, 60, 61, 62, 63, 6
4, 65, 66, 67, 68, 69, 70, 71, 7
2, 73, 75, 79, 80, 81, 82, 83, 8
4, 85, 86, 87, 88, 89, 90, 91, 9
2,95

Test Example 4 Contact Insecticidal Test on P. conch The 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 animals were released, each was covered with a perforated lid, housed in a thermostat at 25 ° C., the number of dead insects after 6 days was investigated, and the mortality was calculated from the same formula as in Test Example 1. Note that the test was performed in a two-section system. As a result, the following compounds showed a mortality of 80% or more.

Compound No. of the present invention: 1, 2, 3, 4, 5,
8, 10, 11, 15, 16, 17, 19, 43, 4
7, 48, 49, 51, 54, 58, 59, 79, 8
0, 84

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

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

Compound No .: 8 of the present invention

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

Compound No. of the present invention: 1, 2, 3, 4, 5,
6, 7, 8, 9, 10, 11, 12, 13, 14, 1
5, 16, 17, 18, 19, 20, 21, 22, 2,
3, 25, 26, 27, 28, 29, 38, 39, 4
1, 43, 45, 46, 47, 48, 49, 50, 5,
1, 54, 55, 58, 59, 60, 61, 62, 6
3, 64, 65, 66, 67, 68, 69, 70, 7
1, 73, 74, 75, 79, 80, 81, 82, 8
3, 84, 85, 88, 89, 90, 91, 92, 9
3, 94

[0389]

The present invention provides a novel insecticide and acaricide with low toxicity and low residue, and an anti-fouling agent for aquatic organisms with little effect on ecosystems and secondary pollution. is there.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 43/824 C07D 401/06 43/832 413/14 43/836 417/06 C07D 401/06 A01N 43 / 82 101A 413/14 103 417/06 104 (72) Inventor Yoshiyuki Kusuoka 722-1, Tsuboi-cho, Funabashi-shi, Chiba Pref., Central Research Laboratory, Nissan Chemical Industry Co., Ltd. Nissan Chemical Industry Co., Ltd., Biological Science Research Institute (72) Inventor Takii Shinji 1470, Shirooka-cho, Shiraoka-cho, Minami-Saitama-gun, Saitama Prefecture Nissan Chemical Industry Co., Ltd. 1470 Nissan Chemical Industries, Ltd. Biological Science Laboratory F-term (reference) 4C063 AA01 AA03 BB03 CC23 CC54 CC62 DD12 DD22 EE03 4H011 AC01 AC03 AC04 AD01 BA01 BA05 BB09 BB10 BC01 BC06 BC17 BC18 BC19 BC20 DA02 DA15 DA16 DD01 DH10

Claims (19)

[Claims] (1) Formula (1):[Wherein Q isEmbedded imageEmbedded imageEmbedded imageAnd A isEmbedded imageEmbedded imageB is H, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl,
C_Two~ C_FourAlkoxyalkyl, CH_ThreeSCH_Two, CH_ThreeO
C_TwoH_FourOCH_Two, Halogen or C₁~ C_FourWith alkyl
C substituted with optionally substituted phenyl₁~ C_FourA
Lucyl, halogen or C₁~ C_FourSubstituted with alkyl
Optionally substituted with benzoyl₁~ C_FourArchi
, Tetrahydropyranyl, (CH_Three)_ThreeSi, C₁~ C_Four
Alkylsulfonyl, halogen or C₁~ C_FourArchi
Phenylsulfonyl optionally substituted with
_TwoCF_Three, C₁~ C_FourMonoalkylaminosulfonyl, C_Two
~ C₈Dialkylaminosulfonyl, phenylaminos
Ruphonyl, C_Two~ C_FiveMonoalkylaminothiocarboni
Le, C_Three~ C₉Dialkylaminothiocarbonyl, C_Two~
C_FiveCyanoalkyl, C_Three~ C₉Alkoxycarbonyla
Lucil, -C (= O) T¹, -P (= O) T^TwoT^Three, -P
(= S) T^TwoT^Three, Alkali metal atoms, alkaline earth metals
Atom or NHT^FourT^FiveT⁶And W isR is halogen, C₁~ C_TenAlkyl, halogen or
Is C₁~ C_FourWith phenyl optionally substituted with alkyl
Replaced C₁~ C_FourAlkyl, 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, C₁~ C₆Alkoxy,
C_Two~ C₆Alkenyloxy, C_Two~ C₆Alkynyloxy
Si, C₁~ C_FourHaloalkoxy, C_Two~ C₆Haloalkenyl
Oxy, C_Two~ C₆Haloalkynyloxy, C₁~ C_FourAl
Killsulfenyl, C₁~ C_FourAlkylsulfinyl, C
₁~ C_FourAlkylsulfonyl, C_Two~ C₆Alkenyl sulf
Enil, C_Two~ C₆Alkenylsulfinyl, C_Two~ C₆A
Lucenylsulfonyl, C_Two~ C₆Alkynylsulfeni
Le, C_Two~ C₆Alkynylsulfinyl, C_Two~ C₆Al
Quinylsulfonyl, C₁~ C_FourHaloalkylsulfeni
Le, C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHalo
Alkylsulfonyl, C_Two~ C₆Haloalkenyl sulfe
Nil, C_Two~ C₆Haloalkenylsulfinyl, C_Two~ C₆
Haloalkenylsulfonyl, C_Two~ C₆Haloalkynyls
Luphenyl, C_Two~ C₆Haloalkynylsulfinyl, C
_Two~ C₆Haloalkynylsulfonyl, NO_Two, CN, -NU¹U
^Two, Phenoxy, OH, naphthyl, C_Two~ C₇Alkoxy
Carbonyl, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FourA
Alkylcarbonyl, C_Two~ C_FiveAlkylcarbonyloxy
Si, C_Two~ C_FiveHaloalkylcarbonyloxy, substituted with Z
Benzoyl, which may be substituted with Z
Phenyl, pyridyl optionally substituted with Z,
Optionally substituted thienyl or -N = CT⁷T⁸In
Or adjacent R or R^TwoTogether with an alkylene group
Ring, 6-membered ring, 7-membered ring or 8-membered ring formed by
A ring, R^TwoIs H, C₁~ C_TenAlkyl, halogen or C₁~
C_FourSubstituted with phenyl optionally substituted with alkyl
C₁~ C_FourAlkyl, C_Two~ C₆Alkenyl, C_Two~
C₆Alkynyl, C₁~ C₆Haloalkyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
Naphthyl, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourA
Lucoxyalkyl, C_Two~ C_FourAlkylcarbonyl, with Z
Optionally substituted benzoyl, substituted with Z
Phenyl, pyridyl optionally substituted with Z, Z
Optionally substituted thienyl or -N = CT⁷T⁸
Or an alkylene group together with adjacent R
, 6-membered, 7-membered or 8-membered ring
Yes, R^ThreeIs H or C₁~ C_TenG is halogen, C₁~ C_TenAlkyl, C₁~ C₆Haloal
Kill, C₁~ C₆Alkoxy, C_Two~ C₆Alkenyloxy
Si, C_Two~ C₆Alkynyloxy, C₁~ C_FourHaloalkoki
Si, C_Two~ C₆Haloalkenyloxy, C_Two~ C₆Haloal
Quinyloxy, C ₁~ 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~ C₇Alkoxy
Carbonyl, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FiveA
Alkylcarbonyl, C_Two~ C_FiveHaloalkylcarbonyl,
C_Two~ C_FiveAlkylcarbonyloxy, C_Two~ C_FiveHaloal
Kill carbonyloxy, C_Three~ C₇Dialkylaminocar
Bonyloxy, phenyl optionally substituted with Z or
Is -N = CT⁷T⁸Or adjacent G or G
¹And a 5-membered ring and a 6-membered ring formed by an alkylene group
A ring, a seven-membered or eight-membered ring, G¹Is H, C₁~ C_TenAlkyl, halogen or C₁~
C_FourSubstituted with phenyl optionally substituted with alkyl
C₁~ C_FourAlkyl, C_Two~ C₆Alkenyl, C _Two~ C₆
Alkynyl, C₁~ C₆Haloalkyl, C₁~ C_ThreeAlkyl
C optionally substituted with_Three~ C₆Cycloalkyl, naph
Chill, C_Two~ C₇Alkoxycarbonyl, C _Two~ C_FourArco
Xyalkyl, C_Two~ C_FourAlkylcarbonyl, substituted with Z
Benzoyl, which may be substituted with Z
Phenyl, pyridyl optionally substituted with Z,
Optionally substituted thienyl or -N = CT⁷T⁸In
Or an alkylene group with adjacent G
A 5-, 6-, 7- or 8-membered ring formed
X is N-X¹, CH-X¹, C- (X¹)_Two, O or S, X¹Is C₁~ C_TenAlkyl, C_Two~ C₆Alkenyl, C_Two~
C₆Alkynyl, C₁~ C₆Haloalkyl, C₁~ C₆Al
Coxy, C_Two~ C₆Alkenyloxy, C_Two~ C₆Alkini
Luoxy, C₁~ C_FourHaloalkoxy, C_Two~ C₆Haloal
Kenyloxy, C_Two~ C₆Haloalkynyloxy, C₁~
C_FourAllyloxy optionally substituted with alkyl, C₁
~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsulf
Inil, C ₁~ C_FourAlkylsulfonyl, C₁~ C_ThreeArchi
C optionally substituted with_Three~ C₆Cycloalkyl, N
O_Two, CN, -NU¹U^Two, OH, C_Two~ C₇Alkoxycarbo
Nil, C_Two~ C_FourAlkoxyalkyl, C_Two~ C_FourAlkyl
Carbonyl, C_Two~ C_FiveHaloalkylcarbonyl, C_Two~
C_FiveAlkylcarbonyloxy, C_Two~ C_FiveHaloalkyl
Carbonyloxy, C_Three~ C₇Dialkylaminocarboni
Substituted with ruoxy, morpholinyl, piperidyl, Z
Benzoyl which may be optionally substituted
Nil, phenoxy optionally substituted with Z or
Pyridyl which may be replaced (provided that X is CH-X¹Ma
Or C- (X¹)_TwoX¹Is C₁~ C_TenAlkyl, C_Two
~ C₆Alkenyl and C₁~ C₆Not a haloalkyl. Ma
X¹When two or more are the same or different
No. ), Y is H, C₁~ C_TenAlkyl, C_Two~ C₆Alkenyl, C_Two
~ C₆Alkynyl, C₁~ C₆Haloalkyl, C₁~ C₆A
Lucoxy, C_Two~ C₆Alkenyloxy, C_Two~ C ₆Archi
Nyloxy, C₁~ C_FourHaloalkoxy, C_Two~ C₆Haloa
Lucenyloxy, C_Two~ C₆Haloalkynyloxy, C₁
~ C_FourAllyloxy optionally substituted with alkyl,
C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
CN, -NU¹U^Two, -C (= O) T¹, C_Two~ C_FourAlkoxy
Alkyl, C_Two~ C_FiveMonoalkylaminothiocarboni
Le, C_Three~ C₉Dialkylaminothiocarbonyl, C_Two~
C₆Alkylthiocarbonyl, morpholinyl, piperidi
, Pyrazolyl optionally substituted with Z, substituted with Z
May be substituted with imidazolyl, Z
Pyrazolinyl, phenyl optionally substituted with Z or
Is pyridyl optionally substituted with Z, or
Is R or R^TwoTogether with 5 formed by an alkylene group
Membered ring, 6-membered ring, 7-membered ring or 8-membered ring (provided that X is
When O, Y is not alkyl or alkoxy. ), X^TwoIs S, O, NR^FourOr CH_Two(However, X^TwoIs two
In the above case, they may be the same or different. ), X^ThreeIs S, O or NR^FourAnd R^FourIs H, C₁~ C_TenAlkyl, halogen or C₁~
C_FourSubstituted with phenyl optionally substituted with alkyl
C₁~ C_FourAlkyl, C_Two~ C₆Alkenyl, C_Two~
C₆Alkynyl, C₁~ C₆Haloalkyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
Naphthyl, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourA
Lucoxyalkyl, C_Two~ C_FourAlkylcarbonyl, with Z
Optionally substituted benzoyl, substituted with Z
Phenyl, pyridyl optionally substituted with Z, Z
Optionally substituted thienyl or -N = CT⁷T⁸
Z is halogen, C₁~ C_FourAlkyl, C₁~ C_FourHaloal
Kill, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy,
C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, C_Two~ C_FiveAl
Kenylsulfenyl, C_Two~ C_FiveAlkenylsulfini
Le, C_Two~ C_FiveAlkenylsulfonyl, C₁~ C_FourHaloal
Killsulfenyl, C₁~ C_FourHaloalkylsulfini
Le, C₁~ C _FourHaloalkylsulfonyl, NO_Two, CN,
CHO, OH, -NU¹U^Two, Phenyl, phenoxy and C_Two
~ C_Five1 to 1 selected from alkoxycarbonyl
5 substituents which may be different from each other,¹Is C₁~ C₂₀Alkyl, C_Two~ C₆Alkenyl, C₁
~ C₆Haloalkyl, C ₁~ C_FourAlkoxy-C₁~ C_FourA
Luquil, C_Three~ C₆Halocycloalkyl, halogen or
Is C₁~ C_FourWith phenyl optionally substituted with alkyl
Replaced C₁~ C_FourAlkyl, C₁~ C_ThreeSubstitute with alkyl
C that may be_Three~ C₆Cycloalkyl and halogen
Or C₁~ C_FourPhenyl optionally substituted with alkyl
Substituted with cycloalkyl, halogen or C₁
~ C_FourPhenyl optionally substituted with alkyl and C₁~
C_FourCyclopropyl and halogen substituted with alkyl
Or C₁~ C_FourFe which may be substituted with alkoxy
C substituted with nyl and halogen_Three~ C_FourCycloalkyl
A group optionally substituted with halogen_Two~ C_FourAlkene
Le and C₁~ C_FourA cyclopropyl group substituted with alkyl,
Halogen or C₁~ C_FourSubstituted with an alkyl group
Phenyl substituted C_Two~ C_FourAlkenyl, C₁
~ C₁₂Alkoxy, C₁~ C_FourHaloalkoxy, C_Two~ C_Five
Alkenyloxy, C₁~ C_ThreeSubstituted with alkyl
Good C_Three~ C₆Cycloalkoxy, benzyloxy, C
_Two~ C_FiveAlkoxycarbonyl, -NU¹U^Two, Phenylami
No, phenyl optionally substituted with Z, substituted with Z
Optionally substituted with phenoxy and Z
Enylthio, naphthyl optionally substituted with Z or
5- or 6-membered heterocyclic ring which may be substituted by Z
Ring groups (however, these heterocyclic groups are thienyl, furyl,
Loryl, oxazolyl, isoxazolyl, thiazolyl,
Isothiazolyl, pyrazolyl, imidazolyl, 1,3
4-oxadiazolyl, 1,2,4-oxadiazoli
1,3,4-thiadiazolyl, 1,2,4-thiazi
Azolyl, 1,2,4-triazolyl, 1,2,3-thio
Asiazolyl, 1,2,3-triazolyl, 1,2,2
3,4-tetrazolyl, pyridyl, pyrimidinyl, pyra
Dinyl, pyridazinyl, 1,3,5-triazinyl,
1,2,4-triazinyl, pyrazolinyl, imidazoly
Nil, oxazolinyl, isoxazolinyl, thiazolini
And 3 (2H) -pyridazinone. )
And T^TwoAnd T^ThreeIs independently OH, phenyl,
C₁~ C₆Alkyl, C₁~ C₆Alkoxy or C₁~ C_Four
Alkylsulfenyl, T^Four, T^FiveAnd T⁶Is independently H, C₁~ C₆Archi
Le, C₁~ C₆Alkenyl, C₁~ C_ThreeSubstituted with an alkyl group
C that may be_Three~ C₆Cycloalkyl group or benzyl
Or T^Four, T^FiveAnd T⁶Two of
Is an oxygen atom together with the nitrogen atom to which each is attached,
5 members which may contain nitrogen atom or sulfur atom
Forming a ring, 6-membered, 7-membered or 8-membered ring group
, T⁷And T⁸Are each independently H, phenyl, benzyl or
Or C₁~ C₆Alkyl or T⁷And T⁸And
5-, 6-, and 7-membered rings with the carbon atoms to which they are attached
Or an 8-membered ring,¹And U^TwoIs independently H, C₁~ C₆Alkyl, C_Two
~ C_FiveWith alkylcarbonyl, phenyl or benzyl
Yes or U¹And U^TwoTogether with the carbon atom to which it is attached
May form a 5-, 6-, 7- or 8-membered ring
L represents the number of methylene, and is 0, 1, 2, or 3.
M represents the number of substituents, and is 0, 1, 2, or 3, n represents the number of substituents, and is 0, 1, 2, 3, or 4.
P represents the number of substituents and is 0, 1 or 2, q represents the number of substituents and 0 or 1 (provided that m, n and
And when p represents an integer of 2 or more, the substituents are the same
They may be different from each other. )] Ethylene derivative
body. 2. The method of claim 2, wherein Q isEmbedded imageEmbedded imageEmbedded imageB is H, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl,
C_Two~ C_FourAlkoxyalkyl, CH_ThreeOC_TwoH_FourOCH_Two,
C₁~ C_FourAlkylsulfonyl, halogen or C₁~
Phenylsulfonii optionally substituted with C4 alkyl
, -SO_TwoCF_Three, C_Two~ C₈Dialkylaminosulfoni
Le, C_Two~ C₉Dialkylaminothiocarbonyl, C_Three~
C₉Alkoxycarbonylalkyl, -C (= O) T¹,
-P (= O) T^TwoT^Three, -P (= S) T^TwoT^Three, Alkali gold
Genus atom, alkaline earth metal atom or NHT^FourT^FiveT⁶so
Yes, R¹Is H, halogen, C₁~ C_TenIf alkyl, halogen
Kuha C₁~ C_FourPhenyl optionally substituted with alkyl
C substituted with₁~ C_FourAlkyl, C_Two~ C₆The alkene
Le, C_Two~ C₆Alkynyl, C₁~ C₆Haloalkyl, C_Two
~ C₆Haloalkenyl, C_Two~ C₆Haloalkynyl, C_Three~
C₆Halocycloalkyl, C₁~ C_ThreeSubstituted with alkyl
May be C_Three~ C₆Cycloalkyl, C₁~ C₆Arco
Kissi, C_Two~ C₆Alkenyloxy, C_Two~ C₆Alkynyl
Oxy, C₁~ C_FourHaloalkoxy, C_Two~ C₆Halo arche
Nyloxy, C_Two~ C₆Haloalkynyloxy, C₁~ C_Four
Alkylsulfenyl, C₁~ C_FourAlkylsulfini
Le, C₁~ C_FourAlkylsulfonyl, C_Two~ C₆Alkenyl
Sulfenyl, C_Two~ C₆Alkenylsulfinyl, C_Two
~ C₆Alkenylsulfonyl, C_Two~ C₆Alkynylsul
Phenyl, C_Two~ C₆Alkynylsulfinyl, C_Two~
C₆Alkynylsulfonyl, C₁~ C_FourHaloalkylsul
Phenyl, C₁~ C_FourHaloalkylsulfinyl, C₁~
C_FourHaloalkylsulfonyl, C_Two~ C₆Haloalkenyl
Sulfenyl, C_Two~ C₆Haloalkenylsulfinyl,
C_Two~ C6 haloalkenylsulfonyl, C_Two~ C₆Haloal
Quinylsulfenyl, C_Two~ C₆Haloalkynyl sulfy
Nil, C_Two~ C₆Haloalkynylsulfonyl, NO_Two, C
N, -NU¹U^Two, Phenoxy, OH, naphthyl, C_Two~ C₇A
Lucoxycarbonyl, C_Two~ C_FourAlkoxyalkyl, C
_Two~ C_FourAlkylcarbonyl, C_Two~ C_FiveAlkyl carboni
Luoxy, C_Two~ C_FiveHaloalkylcarbonyloxy, Z
Benzoyl optionally substituted with
Phenyl, pyridyl optionally substituted with Z
Or thienyl optionally substituted with Z or -N = C
T⁷T⁸Or adjacent R¹Or R^TwoWith
5-, 6-, and 7-membered rings formed by alkylene groups
Or an 8-membered ring (provided that R¹When two or more
It may be one or different. ), R^TwoIs H, C₁~ C_TenAlkyl, halogen or C₁~
C_FourSubstituted with phenyl optionally substituted with alkyl
C₁~ C_FourAlkyl, C_Two~ C₆Alkenyl, C_Two~
C₆Alkynyl, C₁~ C₆Haloalkyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
Naphthyl, C_Two~ C₇Alkoxycarbonyl, C_Two~ C_FourA
Lucoxyalkyl, C_Two~ C_FourAlkylcarbonyl, with Z
Optionally substituted benzoyl, substituted with Z
Phenyl, pyridyl optionally substituted with Z, Z
Optionally substituted thienyl or -N = CT⁷T⁸
Or adjacent R¹Or R^TwoAlong with Alquire
5-, 6-, or 7-membered rings formed by
8-membered ring (however, R^TwoIf two or more are the same or
They may be different from each other. ), Y is H, C₁~ C_TenAlkyl, C_Two~ C₆Alkenyl, C_Two
~ C₆Alkynyl, C₁~ C₆Haloalkyl, C₁~ C₆A
Lucoxy, C_Two~ C₆Alkenyloxy, C_Two~ C ₆Archi
Nyloxy, C₁~ C_FourHaloalkoxy, C_Two~ C₆Haloa
Lucenyloxy, C_Two~ C₆Haloalkynyloxy, C₁
~ C_FourAllyloxy optionally substituted with alkyl,
C₁~ C_FourAlkylsulfenyl, C₁~ C_FourAlkylsul
Finil, C₁~ C_FourAlkylsulfonyl, C₁~ C_ThreeAl
C which may be substituted by kill_Three~ C₆Cycloalkyl,
CN, -NU¹U^Two, -C (= O) T¹, C_Two~ C_FourAlkoxy
Alkyl, C_Two~ C_FiveMonoalkylaminothiocarboni
Le, C_Three~ C₉Dialkylaminothiocarbonyl, C_Two~
C₆Alkylthiocarbonyl, morpholinyl, piperidi
, Pyrazolyl optionally substituted with Z, substituted with Z
May be substituted with imidazolyl, Z
Pyrazolinyl, phenyl optionally substituted with Z or
Is pyridyl optionally substituted with Z, or
Is R¹Or R^TwoTogether with 5 formed by an alkylene group
Membered ring, 6-membered ring, 7-membered ring or 8-membered ring (provided that X is
When O, Y is not alkyl or alkoxy. ), T¹But C₁~ C₂₀Alkyl, C_Two~ C₆Alkenyl, C₁
~ C₆Haloalkyl, C ₁~ C_FourAlkoxy-C₁~ C_FourA
Luquil, C_Three~ C₆Halocycloalkyl, halogen or
Is C₁~ C_FourWith phenyl optionally substituted with alkyl
Replaced C₁~ C_FourAlkyl, C₁~ C_ThreeSubstitute with alkyl
C that may be_Three~ C₆Cycloalkyl and halogen
Or C₁~ C_FourPhenyl optionally substituted with alkyl
Substituted with cycloalkyl, halogen or C₁
~ C_FourPhenyl optionally substituted with alkyl and C₁~
C_FourCyclopropyl and halogen substituted with alkyl
Or C₁~ C_FourFe which may be substituted with alkoxy
C substituted with nyl and halogen_Three~ C_FourCycloalkyl
A group optionally substituted with halogen_Two~ C_FourAlkene
Le and C₁~ C_FourA cyclopropyl group substituted with alkyl,
Halogen or C₁~ C_FourSubstituted with an alkyl group
Phenyl substituted C_Two~ C_FourAlkenyl, C₁
~ C₁₂Alkoxy, C₁~ C_FourHaloalkoxy, C_Two~ C_Five
Alkenyloxy, C₁~ C_ThreeSubstituted with alkyl
Good C_Three~ C₆Cycloalkoxy, benzyloxy, C
_Two~ C_FiveAlkoxycarbonyl, -NU¹U^Two, Phenylami
No, phenyl optionally substituted with Z, substituted with Z
Optionally substituted with phenoxy and Z
Enylthio, naphthyl optionally substituted with Z or
5- or 6-membered heterocyclic ring which may be substituted by Z
Ring groups (however, these heterocyclic groups are thienyl, furyl,
In xazolyl, thiazolyl, pyrazolyl and pyridyl
Selected from. 2. The ethylene derivative according to claim 1, wherein
body. 3. Q is Q-14, Q-15, Q-16,
Q-17, Q-18, Q-19, Q-20, Q-21,
Q-32, Q-33, Q-34, Q-35, Q-36,
Q-37, Q-44, Q-45, Q-46, Q-47,
Q-48, Q-49, Q-50, Q-51, Q-52,
The ethylene derivative according to claim 2, which is Q-53, Q-54, Q-79 or Q-80. 4. Q is Q-18, Q-19, Q-20,
Q-21, Q-32, Q-33, Q-34, Q-35,
Q-36, Q-37, Q-44, Q-45, Q-46,
Q-47, Q-48, Q-49, Q-50, Q-51,
The ethylene derivative according to claim 3, which is Q-52, Q-53, Q-54 or Q-80. 5. Q is Q-18, Q-20, Q-32,
Q-33, Q-34, Q-36, Q-45, Q-46,
Q-47, Q-48, Q-51, Q-53 or Q-5
The ethylene derivative according to claim 4, which is 4. 6. A is A-1, A-2, A-6, A-
9, A-10, A-11, A-12, A-13, A-1
4, A-15, A-16, A-17, A-24, A-2
5, A-26, A-27, A-34, A-38, A-4
The ethylene derivative according to claim 2, which is 4, A-50, A-51, A-52 or A-63. 7. A is A-1, A-2, A-6, A-
9, A-10, A-11, A-12, A-13, A-1
4, A-15, A-16, A-17, A-24, A-2
5, A-26, A-27, A-34, A-36, A-3
8, A-44, A-50, A-51, A-52 or A
The ethylene derivative according to claim 3, which is -63. 8. A is A-1, A-2, A-6, A-
9, A-10, A-11, A-12, A-13, A-1
4, A-15, A-16, A-17, A-24, A-2
5, A-26, A-27, A-34, A-36, A-3
8, A-44, A-50, A-51, A-52 or A
The ethylene derivative according to claim 4, which is -63. 9. A is A-1, A-2, A-6, A-
9, A-10, A-11, A-12, A-13, A-1
4, A-15, A-16, A-17, A-24, A-2
5, A-26, A-27, A-34, A-36, A-3
8, A-44, A-50, A-51, A-52 or A
The ethylene derivative according to claim 5, which is -63. 10. X is an ethylene derivative according to claim 2, wherein the N-X ^1. 11. X is an ethylene derivative according to claim 3, wherein the N-X ^1. 12. X is an ethylene derivative according to claim 4, wherein the N-X ^1. 13. X is an ethylene derivative according to claim 5, wherein the N-X ^1. 14. X is an ethylene derivative according to claim 6, wherein the N-X ^1. 15. X is an ethylene derivative according to claim 7 wherein the N-X ^1. 16. X is an ethylene derivative according to claim 8 wherein the N-X ^1. 17. X is an ethylene derivative according to claim 9 wherein the N-X ^1. 18. A pesticide comprising at least one ethylene derivative according to claim 1 as an active ingredient. 19. An underwater biofouling inhibitor comprising at least one ethylene derivative according to claim 1 as an active ingredient.