JP2000297086A - Heteroarylhydrazone compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound having an excellent pest controlling activity and useful as an agrochemical (pest controlling agent). SOLUTION: This compound is represented by formula I [R1 is a (halogen substituted) 1-6C alkyl, (halogen substituted) 2-6C alkenyl or the like; n and p are each 0-2; R2 and R3 are each H, cyano or the like; A is O, S or the like; Y is a halogen, 2-6C alkenyl or the like; R4 and R5 are each H, a (substituted) 1-6C alkyl or the like; X is a halogen, (halogen substituted) 1-6C alkyl or the like; m is 1-5], e.g. 4-chlorophenyl=5-ethylthiomethylthiophen-2-yl=ketone=N- methoxycarbonylhydrazone. The compound of formula I is produced, for example, by reacting at -10 deg.C to the reflux temperature in the reaction system for 0.5-48 h (A) a carbonyl compound of formula II with (B) a hydrazine compound of formula III at 1.0-20.0 mol per mol of the component A in the presence of (C) an acid if necessary, and in (D) a solvent if necessary.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel heteroarylhydrazone compound having excellent pest control activity or a salt thereof, a method for producing them, an agricultural chemical (pesticide) containing them as an active ingredient or a pesticide. Regarding those intermediates.

[0002]

2. Description of the Related Art In recent years, existing commercial pest control agents include:
Due to problems such as residue, accumulation, environmental pollution, etc., there are some drugs whose use is regulated or whose efficacy is reduced due to generation of resistant pests by long-term use. Therefore, there is a demand for a safe pest control agent which has high activity against these resistant pests and which does not harm humans, livestock, the environment and the like.

[0003] JP-A-1-501935 describes a heteroarylhydrazone compound, but its pest control activity is low and insufficient. Further, the publication does not disclose or suggest a heteroaryl hydrazone compound in which a sulfur-containing methyl group is bonded to a heterocycle.

[0004]

DISCLOSURE OF THE INVENTION The present inventors have made intensive studies on heteroaryl hydrazone compounds for many years,
The inventors have found that certain heteroarylhydrazone compounds have excellent pest control activity, and have completed the present invention.

[0005]

The present invention provides a compound represented by the following general formula (I):

[0006]

Embedded image [Wherein, R ¹ is a C ₁ -C ₆ alkyl group (the alkyl group may be substituted with the same or different 1 to 5 halogen atoms), a C ₂ -C ₆ alkenyl group (the The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C ₂
-C ₆ alkynyl group, phenyl group ｛The phenyl group is
1 to 5 identical or different halogen atoms, C ₁
A C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is the same or different 1 to 5 halogen atoms) May be substituted with 5 halogen atoms) or a cyano group. {Or 5- or 6-membered heterocyclic group} The heterocyclic group contains at least one nitrogen atom, oxygen atom or sulfur atom and is the same or different from 1 to 3
Halogen atoms, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is Same or different 1 to 5
May be substituted by halogen atoms. ) Or a cyano group. ｝, And n is
0, 1 or 2; R ² and R ³ are the same or different and each represent a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halogen atom or a cyano group, or
R ² and R ³ are taken together with the carbon atoms to which they are bonded to form a C ₃ -C ₇ cycloalkyl group, wherein the cycloalkyl group is the same or different and has 1 to 5 C ₁ -C ₆ alkyl groups ( The alkyl group may be substituted with the same or different 1 to 5 halogen atoms.), C
₂ -C ₆ alkenyl group (said alkenyl group is the same or different 1 to 3 halogen atoms may be substituted.), C ₁ -C ₆ alkoxy group (said alkoxy group has the same or different 1 Or 5 or more halogen atoms.) Or a halogen atom. Wherein A is an oxygen atom, a sulfur atom or a group of the formula NR ⁶ , wherein R is
⁶ is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), C _2-
A C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ alkoxy group (the alkoxy group may be substituted by the same or different 1 to 5 halogen atoms), C ₂ -C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₆ alkylthio group (the alkylthio group may be substituted by the same or different 1 to 5 halogen atoms), phenyl group, It represents a phenoxy group, a phenylthio group, a formyl group, a C ₂ -C ₆ alkylcarbonyl group, a nitro group or a cyano group. Represents p, p represents 0, 1 or 2, Y represents a halogen atom, a C ₁ -C ₆ alkyl group (the alkyl group is the same or different and is substituted by 1 to 5 halogen atoms, good.), C ₂ ~C ₆ alkenyl, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group (said alkoxy group may be substituted by same or different 1 to 5 halogen atoms .), C ₂ ~C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₆ alkylthio group (said alkylthio group may be substituted by same or different 1 to 5 halogen atoms Good)), a phenyl group, a phenoxy group, a phenylthio group,
Formyl, C ₂ -C ₆ alkylcarbonyl group, a nitro group or a cyano group, when p is 2, each of the plurality of Y may be the same or different, R ⁴ and R ⁵ are the same or different, Hydrogen atom, C ₁ -C ₆ alkyl group (the alkyl group may be the same or different 1 to 5 halogen atoms or one C ₁ -C ₆ alkoxy group, C ₁ -C ₆
It may be substituted by an alkylthio group, a C ₂ -C ₇ alkoxycarbonyl group, a pyridyloxy group, a cyano group or a hydroxyl group. ), C ₂ -C ₆ alkenyl group (said alkenyl group may be substituted by 1 to 3 identical or different halogen atoms.), C ₂ ~C ₆ alkynyl group, a formyl group, C ₂ -C ₁₀ alkylcarbonyl groups ｛The alkylcarbonyl groups may be the same or different 1 to 5 halogen atoms or one C ₁ -C ₆ alkoxy group, phenoxy group (the phenoxy group may be the same or different 1 to 5 C ₁ -C ₆ alkyl group, C ₁ -C ₆
It may be substituted by an alkoxy group or a halogen atom. ), A C ₁ -C ₆ alkylthio group, a phenylthio group (the phenylthio group is substituted with _{1 to} 5 identical or different C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. good.), a carboxyl group, may be substituted by C ₂ -C ₇ alkoxycarbonyl group or a cyano group. ｝, C ₃ -C ₇ alkenylcarbonyl group (the alkenylcarbonyl group may be substituted by the same or different 1 to 5 halogen atoms or 1 phenyl group or C ₂ -C ₇ alkoxycarbonyl group. ), C ₃ -C ₇ alkynylcarbonyl group, benzoyl group (the benzoyl group may be the same or different 1 to 5 halogen atoms or C ₁ -C ₆
Alkyl group or one carboxyl group or C ₂ -C ₇
It may be substituted by an alkoxycarbonyl group. ), A pyridylcarbonyl group (the pyridylcarbonyl group may be substituted by the same or different 1 to 4 halogen atoms or a C _{1 to} C ₆ alkyl group), a thienylcarbonyl group (the thienylcarbonyl group is May be substituted by the same or different 1 to 3 halogen atoms or C ₁ -C ₆ alkyl groups), C ₂ -C ₇ alkyl (thiocarbonyl) group {-C
(= S)-{, phenyl (thiocarbonyl) group} -C
(= S)-｝, C ₂ -C ₇ alkoxycarbonyl group (the alkoxycarbonyl group may be the same or different 1 to 5 halogen atoms or one C ₁ -C ₆ alkoxy group, C ₁ -C ₆ the alkylthio group or a cyano group may be substituted.), C ₃ ~C ₇ alkenyloxycarbonyl group, a phenoxycarbonyl group (said phenoxycarbonyl group may be the same or different 1 to 5 halogen atoms or C ₁ -C _6- alkyl group), C ₂ -C ₇ (alkylthio) carbonyl group ｛-
S—C (＝ O)-｝, (phenylthio) carbonyl group,
C ₂ -C ₇ alkyl dithio group, a phenyl dithio group, C ₃ -C ₈ alkylcarbonyl group, phenylcarbonyl group, C ₃ -C ₈ alkoxycarbonyl group, a phenoxycarbonyl group, an amino group {said The aminocarbonyl group may be the same or different one or two C ₁ -C ₆ alkyl groups, C ₂ -C ₇ alkoxycarbonyl groups, (C ₂ -C ₆
C ₇ alkoxycarbonyl) C ₁ -C ₆ alkyl group or a
Phenyl groups (the phenyl groups may be substituted with the same or different 1 to 5 halogen atoms). ｝, An aminothiocarbonyl group (the aminothiocarbonyl group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups), a furanylcarbonyl group (the furanylcarbonyl group is may be substituted by 1 to 3 identical or different halogen atoms.), pyrazolyl group (the pyrazolyl group may be the same or different 1 or 2 C ₁ -C ₆ alkyl group or a halogen atom May be substituted.), C _1-
C ₆ alkylsulfonyl group, phenylsulfonyl group (the phenylsulfonyl group may be substituted by the same or different 1 to 5 C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. ) Or an aminosulfonyl group (the aminosulfonyl group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups), or R ⁴ and R ⁵ together And a methylidene group {the methylidene group may be the same or different and one or two C ₁ -C ₆ alkyl groups (the alkyl group may be substituted with the same or different 1 to 5 halogen atoms. ), phenyl group (said phenyl group are the same or are selected from the group consisting of C ₁ -C ₆ alkyl group, a halogen atom and C ₁ -C ₆ alkoxy group By 1 to 5 substituents which became may be substituted.), A halogen atom, C ₂ -C ₇ alkoxycarbonyl group, phenoxycarbonyl group or amino group {said amino group may be the same or different 1 or 2 C ₁
-C ₆ alkyl group or (C ₁ -C ₆ alkoxy) C ₁ -C ₆
It may be substituted by an alkyl group. ｝ May be substituted. Or R ⁴ and R ⁵ together with the nitrogen atom to which they are attached form succinimide, phthalimide or pyrrole-2,5-dione;
Halogen atom, C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), C ₁ -C ₆ alkoxy group (the alkoxy group is the same Or different 1 to 5
May be substituted by halogen atoms. ), C ₂
-C ₇ alkoxycarbonyl group or (C ₁ -C ₆ alkyl) aminocarbonyl group (said alkylaminocarbonyl group, the same or different 1 to 5 halogen atoms may be substituted.) Indicates, m is 1,
2, 3, 4 or 5 is indicated. A heteroarylhydrazone compound or a salt thereof, a pesticide containing the same as an active ingredient, the following general formula (II):

[0007]

Embedded image [Wherein, R ² , R ³ , p, A, Y, X and m have the same meanings as described above, and R ⁷ represents a hydrogen atom, a halogen atom, a mercapto group, a hydroxyl group, a C ₂ -C ₇ alkylcarbonylthio. Group, C
₁ -C ₆ alkylsulfonyloxy group, C ₆ -C ₁₀ arylsulfonyloxy group (such arylsulfonyloxy groups may be substituted by same or different 1 to 5 substituents C ₁ -C ₆ alkyl group.) , An amidinosulfenyl group or a group represented by the formula SO _n R ¹ (wherein, R ¹ has the same meaning as described above). A heteroarylcarbonyl compound represented by the following general formula (III):

[0008]

Embedded image [In the formula, R ² , R ³ , R ⁴ , R ⁵ , p, A, Y, X and m have the same meanings as described above, and R ^7a represents a hydrogen atom, a halogen atom, a mercapto group, a hydroxyl group, a C ₂ -C ₇ alkylcarbonyl thio group, C ₁ -C ₆ alkylsulfonyloxy group, C ₆
-C ₁₀ arylsulfonyloxy group (such arylsulfonyloxy groups may be the same or by different 1 to 5 substituents C ₁ -C ₆ alkyl group may be substituted.) Showing a or amidinophenyl sulfenyl group. And a method for producing the same.

In the present invention, "C ₁ -C ₆ alkyl group"
Is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl,
Pentyl, 2-methylbutyl, 1-methylpentyl, neopentyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, cyclopropyl,
It is a linear or branched or cyclic alkyl group having 1 to 6 carbon atoms such as cyclobutyl, cyclopentyl or cyclohexyl, preferably a linear or branched or cyclic alkyl group having 1 to 4 carbon atoms (C ₁ To C ₄ alkyl group)
And more preferably a linear or branched alkyl group having 1 to 3 carbon atoms (C ₁ -C ₃ alkyl group), and even more preferably a methyl group or an ethyl group.

In the present invention, “halogen atom” is
For example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a fluorine atom or a chlorine atom, even more preferably, It is a chlorine atom.

In the present invention, the term "C ₁ -C ₆ alkyl group substituted by 1 to 5 identical or different halogen atoms" includes, for example, chloromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, -Chloroethyl, 1-chloropropyl, 3-chloropropyl, 1
-Chlorobutyl, 4-chlorobutyl, 6-chlorohexyl, fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl,
Same or different like 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, 1,1,2,2,2-pentafluoroethyl, fluorochloromethyl, bromomethyl, 2-bromoethyl, iodomethyl 1 to 5 of the above “halogen atoms” are groups bonded to the above “C ₁ -C ₆ alkyl group”, and preferably 1 to 5 identical or different fluorine or chlorine atoms are
₁ -C is ₄ alkyl group "bonded to group, and more preferably, the same or different 1 to 5 fluorine atoms or chlorine atoms 1 carbon atoms or two alkyl groups (C ₁ -C ₂ alkyl Group), even more preferably, chloromethyl, difluoromethyl, trifluoromethyl,
2,2,2-trifluoroethyl or 1,1,2,2
2-pentafluoroethyl group.

In the present invention, the "C ₂ -C ₆ alkenyl group" includes, for example, vinyl, 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,
2 to 6 carbon atoms such as -butenyl, 2-butenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 1-hexenyl, 5-hexenyl Linear or branched alkenyl groups, preferably a linear or branched alkenyl group having 2 to 4 carbon atoms (C ₂ -C ₄ alkenyl group), more preferably 2-propenyl Group.

In the present invention, "C ₂ -C ₆ alkenyl group substituted by 1 to 3 identical or different halogen atoms" means, for example, 2-chlorovinyl, 3-chloro-2-propenyl, , 2-dichlorovinyl, 2-
Chloro-2-fluorovinyl, 3,3-dichloro-2-
The same or different “halogen atoms” such as propenyl, 3-bromo-2-propenyl, 3-iodo-2-propenyl, 2,3,3-trichloro-2-propenyl
1 to 3 are groups bonded to the above “C ₂ -C ₆ alkenyl group”, and preferably, one or two same or different fluorine or chlorine atoms are the above “C ₂ -C ₄ alkenyl group”. "
Is a group bonded to

In the present invention, "C ₂ -C ₆ alkynyl group" includes, for example, ethynyl, 2-propynyl, 1-methylpropynyl, 2-butynyl, 2-pentynyl, 2-pentynyl,
A straight-chain or branched alkynyl group having 2 to 6 carbon atoms such as hexynyl and 5-hexynyl; preferably a straight-chain or branched alkynyl group having 2 to 4 carbon atoms (C ₂ -C ₄ alkynyl group); ), And more preferably a 2-propynyl group.

In the present invention, "C ₁ -C ₆ alkoxy" means, for example, methoxy, ethoxy, propoxy,
Isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, isopentoxy,
-Methylbutoxy, neopentoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 3,3
-Dimethylbutoxy, 1,1-dimethylbutoxy, 1,
A linear or branched alkoxy group having 1 to 6 carbon atoms such as 2-dimethylbutoxy and 2-ethylbutoxy;
It is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms (C ₁ -C ₄ alkoxy group), and more preferably an alkoxy group having 1 or 2 carbon atoms (C ₁ -C ₂ alkoxy group). Alkoxy group).

In the present invention, "a C ₁ -C ₆ alkoxy group substituted by 1 to 5 identical or different halogen atoms" means, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, 1-chloroethoxy,
2-chloroethoxy, 3-chloropropoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2 , 2-pentafluoroethoxy, 2-bromoethoxy, 3-chloropropoxy, 4
1 to 5 identical or different “halogen atoms” such as chlorobutoxy and iodomethoxy
_{1 to} C ₆ alkoxy group ''.
A group in which the same or different 1 to 5 fluorine atoms or chlorine atoms are bonded to the above-mentioned “C ₁ -C ₄ alkoxy group”, more preferably the same or different 1 to 3 fluorine atoms or chlorine atoms An atom is a group bonded to the aforementioned “C ₁ -C ₂ alkoxy group”, even more preferably, trifluoromethoxy, difluoromethoxy or chloromethoxy.

In the present invention, "1 to 5 identical or different halogen atoms, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by 1 to 5 identical or different halogen atoms, .), C ₁ -C ₆ alkoxy group (said alkoxy group may be the same or different 1 to 5 by halogen atoms may be substituted.) or has been the phenyl group "substituted by a cyano group, for example, The “halogen atom” and the “C ₁ -C ₆ alkyl” such as chlorophenyl, fluorophenyl, methylphenyl, hexylphenyl, trifluoromethylphenyl, pentafluoromethylethylphenyl, methoxyphenyl, trifluoromethoxyphenyl and cyanophenyl Group ", said" the same or different 1 to 5 halogen atoms Conversion has been C ₁ -C ₆ alkyl group ",
The "C ₁ -C ₆ alkoxy group", C ₁ substituted the by 'the same or different 1 to 5 halogen atoms
A phenyl group substituted by the same or different 1 to 5 substituents selected from the group consisting of -C ₆ alkoxy group "and cyano group, preferably a fluorine atom, a chlorine atom, a bromine atom, A phenyl group substituted by 1 to 3 identical or different substituents selected from the group consisting of “C ₁ -C ₂ alkyl group”, “C ₁ -C ₂ alkoxy group” and cyano group; More preferably, it is fluorophenyl, chlorophenyl, methylphenyl, trifluoromethylphenyl, methoxyphenyl or cyanophenyl.

In the present invention, "a 5- or 6-membered heterocyclic group containing at least one nitrogen, oxygen or sulfur atom" includes, for example, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl Containing 1 to 4 nitrogen, oxygen or sulfur atoms such as thiazolyl, isothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyridyl, pyrimidinyl, pyrazinyl and pyridazinyl
Or a 6-membered heterocyclic group, preferably a nitrogen atom,
A 5- or 6-membered heterocyclic group containing 1 to 3 oxygen or sulfur atoms, more preferably a nitrogen atom,
It is a 5- or 6-membered heterocyclic group containing one or two oxygen or sulfur atoms, even more preferably a furyl, thienyl, pyrazolyl, imidazolyl, isoxazolyl, thiazolyl or triazolyl group.

In the present invention, "1 to 3 identical or different halogen atoms, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by 1 to 5 identical or different halogen atoms, .), C ₁ -C ₆ alkoxy group (said alkoxy group is the same or different 1 to 5 halogen atoms may be substituted.) or substituted by a cyano group, at least one nitrogen atom, The "5- or 6-membered heterocyclic group containing an oxygen atom or a sulfur atom" is the above-mentioned "halogen atom",
The "C ₁ -C ₆ alkyl group", C ₁ ~ substituted the by 'the same or different 1 to 5 halogen atoms
A C ₆ alkyl group ”, the aforementioned“ C ₁ -C ₆ alkoxy group ”, 1 to 5 identical or different“ halogen atoms ”
The same or different ones selected from the group consisting of the above-mentioned “C ₁ -C ₆ alkoxy group” and a cyano group substituted by
And the above-mentioned "5- or 6-membered heterocyclic group containing at least one nitrogen atom, oxygen atom or sulfur atom" to which three substituents are bonded, preferably a fluorine atom, a chlorine atom, a bromine atom A nitrogen atom substituted by the same or different 1 or 2 substituents selected from the group consisting of the aforementioned “C ₁ -C ₂ alkyl group”, the aforementioned “C ₁ -C ₂ alkoxy group” or a cyano group, One oxygen or sulfur atom
Or a 5- or 6-membered heterocyclic group containing 1 to 3 or more preferably 1 or 2 identical or different members selected from the group consisting of a fluorine atom, a chlorine atom, a methyl group, a methoxy group and a cyano group Is a furyl, thienyl, pyrazolyl, imidazolyl, isoxazolyl, thiazolyl or triazolyl group to which the above substituent is bonded.

In the present invention, “C ₃ -C ₇ cycloalkyl group” includes, for example, cyclopropyl, cyclobutyl,
A cyclopentyl, cyclohexyl or cycloheptyl group, preferably a cyclopropyl, cyclopentyl or cyclohexyl group.

In the present invention, “1 to 5 identical or different C ₁ -C ₆ alkyl groups (the alkyl groups are
It may be substituted by the same or different 1 to 5 halogen atoms. ), A C ₂ -C ₆ alkenyl group (the alkenyl group may be substituted by the same or different 1 to 3 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is the same or the different 1 to 5 halogen atoms may be substituted.) or a C ₃ -C ₇ cycloalkyl group "substituted by a halogen atom, the aforementioned" C ₁ -C ₆ alkyl group ", the" identity or different 1 to 5 substituents C ₁ -C ₆ alkyl group substituted by a halogen atom ", the" C ₂ -C ₆
Alkenyl group ", the same" the same or different 1 to 3
Pieces C ₂ -C ₆ alkenyl group substituted by halogen atoms ", the" C ₁ -C ₆ alkoxy group ", C ₁ substituted the by 'the same or different 1 to 5 halogen atoms -C ₆ alkoxy group "and the substituted by 1 to 5 substituents selected from the group consisting of the" halogen atom "is" C ₃ -C ₇ cycloalkyl group ", preferably, the" C ₁ -C ₂ alkyl groups ", the above-mentioned" C ₁ -C ₂ alkyl groups "substituted by the same or different 1 to 5 fluorine atoms or chlorine atoms, the above" C ₂ -C ₄ alkenyl groups ", the same or different 1 Or the “C ₂ -C ₄ alkenyl group” substituted by two fluorine atoms or chlorine atoms, the “C ₁ -C ₂ alkoxy group”, the same or different one or two fluorine atoms or chlorine atoms Replace The aforementioned "C ₁ -C ₂ alkoxy group" fluorine atom,
1 to 3 selected from the group consisting of chlorine atom or bromine atom
Cyclopropyl, cyclopentyl or cyclohexyl group substituted by two substituents, more preferably 1 selected from the group consisting of methyl, ethyl, trifluoromethyl, methoxy, chlorine and fluorine.
Or a cyclopropyl, cyclopentyl or cyclohexyl group substituted by two substituents.

In the present invention, the "C ₂ -C ₆ alkenyloxy group" is, for example, allyloxy, 2-butenyl-
1-oxy, 3-butenyl-2-oxy, 2-pentenyl-1-oxy, 3-butenyl-1-oxy, 5-hexenyl-1-oxy, 4-pentenyl-1-oxy,
-Butenyl-1-methyl-1-oxy, 2-methyl-2
A straight-chain or branched-chain alkenyloxy group having 2 to 6 carbon atoms such as -propenyl-1-oxy and 2-methyl-3-butenyl-2-oxy, preferably having 3 to 5 carbon atoms. It is a linear or branched alkenyloxy group, more preferably an allyloxy group.

In the present invention, "C ₂ -C ₆ alkynyloxy group" means, for example, propargyloxy, 3-butyn-2-oxy, 2-methyl-3-butyn-2-oxy, 2-butyn-1 2 to 6 carbon atoms such as -oxy, 2-pentyne-1-oxy and 2-hexyne-1-oxy
Straight-chain or branched-chain alkynyloxy groups, preferably a straight-chain or branched-chain alkynyloxy group having 3 to 5 carbon atoms, more preferably a propargyloxy group.

In the present invention, the "C ₁ -C ₆ alkylthio group" includes, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylite, sec-butylthio, tert-butylthio, pentylthio, 2-methylbutylthio , 1-methylpentylthio,
A straight chain having 1 to 6 carbon atoms such as neopentylthio, hexylthio, 1-methylhexylthio, 3,3-dimethylbutylthio, 2,2-dimethylbutylthio, cyclopropylthio, cyclopentylthio, cyclohexylthio, a branched or cyclic alkylthio group, preferably a linear or branched alkylthio group having 1 to 4 carbon atoms (C ₁ -C ₄ alkylthio group), more preferably, is a methylthio or ethylthio group .

In the present invention, “a C ₁ -C ₆ alkylthio group substituted by 1 to 5 identical or different halogen atoms” means that 1 to 5 identical or different “halogen atoms” are the same as those described above. A C ₁ -C ₆ alkylthio group ”; preferably, the above-mentioned“ C ₁ -C ₆ alkylthio group ”substituted by ₁ to 5 identical or different chlorine or fluorine atoms.
A C ₄ alkylthio group, more preferably a chloromethylthio, dichloromethylthio or trifluoromethylthio group.

In the present invention, "C_Two~ C₇Alkoxyka
"Rubonyl group" means, for example, methoxycarbonyl, ethoxy
Xycarbonyl, propoxycarbonyl, cyclopropo
Xoxycarbonyl, butoxycarbonyl, sec-butoxyca
Rubonyl, isobutoxycarbonyl, cyclobutoxyca
Rubonyl, tert-butoxycarbonyl, pentoxycal
Bonyl, pentyl-2-oxycarbonyl, 2,2-di
Methyl-1-oxycarbonyl, pentyl-3-oxy
Carbonyl, cyclopentoxycarbonyl, hexylo
Xycarbonyl and cyclohexyloxycarbonyl
Linear or branched or cyclic alkyl groups having 2 to 7 carbon atoms
Alkoxycarbonyl group, preferably having 2 to 2 carbon atoms.
5 straight or branched or cyclic alkoxy carbonyls
Group (C _Two~ C_FiveAlkoxycarbonyl group)
Preferably, a straight or branched chain having 2 to 4 carbon atoms or
A cyclic alkoxycarbonyl group, even more preferably
It is a methoxycarbonyl or ethoxycarbonyl group.

In the present invention, "a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, a C ₂ -C ₇ alkoxycarbonyl group, a pyridyloxy group, a cyano group or a C ₁ -substituted hydroxyl group" -C ₆ the alkyl group ", the" C ₁ -C ₆ alkoxy group ", the" C ₁ -C ₆ alkylthio group ", the" C ₂ -C ₇ alkoxycarbonyl group ", pyridyloxy group, a cyano group or The “C ₁ -C ₆ alkyl group” having one hydroxyl group bonded thereto, preferably the “C ₁ -C ₆ alkyl group”
₁ -C ₄ alkoxy group ", the" C ₁ -C ₄ alkylthio group ", the" C ₂ -C ₅ alkoxycarbonyl group ", pyridyloxy group, the cyano group or a hydroxyl group is bonded one" C ₁ -C ₄ alkyl group ", more preferably a methoxy group, an ethoxy group, a methylthio group, a methoxycarbonyl group, an ethoxycarbonyl group, a pyridyloxy group or a cyano group to which one" C ₁ -C ₂ alkyl group "is bonded. It is.

In the present invention, “C ₂ -C ₁₀ alkylcarbonyl group” means, for example, acetyl, propionyl,
Propylcarbonyl, isopropylcarbonyl, cyclopropylcarbonyl, butylcarbonyl, sec-butylcarbonyl, isobutylcarbonyl, tert-butylcarbonyl, cyclobutylcarbonyl, pentylcarbonyl,
Carbon such as pentyl-2-carbonyl, 2,2-dimethyl-1-propylcarbonyl, cyclopentylcarbonyl, hexylcarbonyl, cyclohexylcarbonyl, 4-methylcyclohexylcarbonyl, 1-methylcyclohexylcarbonyl, heptylcarbonyl, octylcarbonyl, nonylcarbonyl A linear or branched or cyclic alkylcarbonyl group having 2 to 10 carbon atoms, preferably a linear or branched or cyclic alkylcarbonyl group having 2 to 8 carbon atoms (C ₂ -C ₈ alkylcarbonyl group) And more preferably a straight-chain or branched-chain or cyclic alkylcarbonyl group having 2 to 6 carbon atoms (C
A ₂ -C ₆ alkylcarbonyl group), still more preferably, acetyl, propionyl, propylcarbonyl, cyclopropylcarbonyl or butyl group.

In the present invention, the term “phenoxy group substituted by _{1 to} 5 identical or different C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms” refers to the aforementioned “C ₁ -C ₆ -alkyl group”. A phenoxy group in which 1 to 5 identical or different substituents selected from the group consisting of a “C ₆ alkyl group”, the “C ₁ -C ₆ alkoxy group” and the “halogen atom” are bonded to a benzene ring. preferably, the "C ₁ -C ₂ alkyl group", the "C ₁ -C ₂ alkoxy group", a fluorine atom, the same or different 1 to 3 selected from the group consisting of chlorine and bromine Is a phenoxy group bonded to a benzene ring, more preferably a methylphenoxy group, a methoxyphenoxy group, a fluorophenoxy group or a chlorophenoxy group.

In the present invention, "a phenylthio group substituted by _{1 to} 5 identical or different C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms"
Means that the same or different 1 to 5 substituents selected from the group consisting of the “C ₁ -C ₆ alkyl group”, the “C ₁ -C ₆ alkoxy group” and the “halogen atom” are benzene A phenylthio group bonded to the ring, preferably
The same or different 1 to 3 substituents selected from the group consisting of the “C ₁ -C ₂ alkyl group”, the “C ₁ -C ₂ alkoxy group”, a fluorine atom, a chlorine atom and a bromine atom are benzene; A phenylthio group bonded to a ring, more preferably, a methylphenylthio group, a methoxyphenylthio group, a fluorophenylthio group or a chlorophenylthio group.

In the present invention, “1 to 5 identical or different halogen atoms or one C _{1 to} C ₆ alkoxy group, phenoxy group (the phenoxy group is the same or different 1 to 5 C ₁ -C ₆ alkyl group, C ₁ -C ₆
It may be substituted by an alkoxy group or a halogen atom. ), A C ₁ -C ₆ alkylthio group, a phenylthio group (the phenylthio group is substituted by the same or different 1 to 5 C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. Good)), a carboxyl group, a C ₂ -C ₇ alkoxycarbonyl group or a C ₂ -C ₁₀ alkylcarbonyl group substituted by a cyano group ”is the same or different from one to five of the above“ halogen atoms ”or 1 Of the above “C ₁ -C ₆ alkoxy groups”, phenoxy groups, and “the same or different 1 to 5 C
₁ -C ₆ alkyl group, a phenoxy group substituted by C ₁ -C ₆ alkoxy group or halogen atom "," the "C ₁ ~
C ₆ alkylthio group ", a phenylthio group, the" same or different 1 to 5 substituents C ₁ -C ₆ alkyl group, C ₁
A phenylthio group substituted by a C ₆ alkoxy group or a halogen atom, a carboxyl group, the C _{2 to} C ₇ alkoxycarbonyl group, or the C _{2 to} C ₁₀ alkylcarbonyl group to which a cyano group is bonded, Preferably, the same or different one to three fluorine or chlorine atoms or one of the above “C ₁ -C ₄ alkoxy group”, phenoxy group, the above “C ₁ -C ₄ alkylthio group”, a phenylthio group, carboxyl group, the "C ₂ ~
A C ₅ -alkoxycarbonyl group ”or a C ₂ -C ₁₀ alkylcarbonyl group to which a cyano group is bonded, even more preferably 1 to 3 identical or different fluorine or chlorine atoms or 1 methoxy group, The above-mentioned “C ₂ -C ₁₀ alkylcarbonyl group” to which an ethoxy group, a phenoxy group, a methylthio group, an ethylthio group or a cyano group is bonded, particularly preferably 1 to 3 identical or different chlorine atoms or 1 Acetyl, propionyl, propylcarbonyl, cyclopropylcarbonyl or butylcarbonyl group to which a methoxy group, phenoxy group, methylthio group or cyano group is bonded.

In the present invention, "C ₃ -C ₇ alkenylcarbonyl group" means acryloyl, 2-butenoyl, methylacryloyl, 3-butenoyl, 2-pentenoyl, 4-pentenoyl, 2-methyl-2-butenoyl,
A straight-chain or branched-chain or cyclic having 3 to 7 carbon atoms such as 3-methyl-2-butenoyl, 1-cyclohexenecarbonyl, 1-cyclopentenecarbonyl, 2-hexenoyl, 5-hexenoyl, 1-heptenoyl and 6-heptenoyl An alkenylcarbonyl group, preferably
Straight or branched chain or cyclic alkenyl group having 3 to 5 carbon (C ₃ -C ₅ alkenyl group)
And more preferably a chain alkenylcarbonyl group having 3 or 4 carbon atoms (C ₃ -C ₄ alkenylcarbonyl group)
And even more preferably a propenylcarbonyl group.

In the present invention, "C ₁ -C ₅ substituted with 1 to 5 halogen atoms or 1 phenyl group or C ₂ -C ₇ alkoxycarbonyl group"
₃ and -C ₇ alkenylcarbonyl group ", for example, 2-chloro-acryloyl, 1-chloro-acryloyl, 2-bromo acryloyl, 2-fluoro-acryloyl, 2-phenyl-acryloyl, 1-phenyl-acryloyl, 3- chloro 2- butenoyl, 4-chloro-3-butenoyl,
5,5-dichloro-4-pentenoyl, 2-methoxycarbonyl-acryloyl, 3-hexyloxy-2- aforementioned "halogen atom" such as butenoyl 1 to 5 or one phenyl group or the "C ₂ -C "C ₃ -C ₇ alkenylcarbonyl group" to which a " ₇ alkoxycarbonyl group" is bonded, preferably 1 to 5 identical or different fluorine or chlorine atoms or 1 to 5
Phenyl groups or the above-mentioned “C ₃ -C ₅ alkenylcarbonyl group” to which the “C ₂ -C ₅ alkoxycarbonyl group” is bonded, more preferably 1 to 3 identical or different fluorine atoms or The above-mentioned “C ₃ -C ₄ alkenylcarbonyl group” having a chlorine atom or one phenyl bonded thereto, still more preferably a propenylcarbonyl group having one chlorine atom or a phenyl group bonded thereto.

In the present invention, the "C ₃ -C ₇ alkynylcarbonyl group" includes, for example, ethynylcarbonyl, 1-
Propinoylcarbonyl, 2-propinoylcarbonyl, 3-butynylcarbonyl, 4-pentinoylcarbonyl, 5-hexinoylcarbonyl, 1-methyl-2-
A linear or branched alkynylcarbonyl group having 3 to 7 carbon atoms, such as propinoylcarbonyl or 1,1-dimethyl-2-propinoylcarbonyl; preferably a linear or branched alkynylcarbonyl group having 3 to 5 carbon atoms; It is a chain alkynylcarbonyl group, more preferably an alkynylcarbonyl group having 3 or 4 carbon atoms.

In the present invention, "a benzoyl group substituted by 1 to 5 identical or different halogen atoms or C ₁ -C ₆ alkyl groups or one carboxyl group or C ₂ -C ₇ alkoxycarbonyl group" Is the same or different 1 to 5 substituents selected from the group consisting of the “halogen atom” and the “C ₁ -C ₆ alkyl group”, or the “carboxyl group” or the “C ₂ -C 6 ₇ alkoxycarbonyl group "is a benzoyl group bonded to the benzene ring, preferably, fluorine atom, chlorine atom, different same or selected from a bromine atom and the group consisting of the" C ₁ -C ₄ alkyl group "1 or a 5 substituents, a carboxyl group or a benzoyl group wherein the "C ₂ -C ₅ alkoxycarbonyl group" bonded, more preferably, Mono- or different 1 to 5 chlorine atoms or fluorine atoms are benzoyl group bonded to the benzene ring, even more preferably more, a benzoyl group one to five chlorine atom is bonded to a benzene ring.

In the present invention, the “pyridylcarbonyl group substituted by the same or different 1 to 4 halogen atoms or C _{1 to} C ₆ alkyl groups” includes the above “halogen atom” and the above “C _{1 to} C 6 ₆ alkyl groups "is a pyridylcarbonyl group having 1 to 4 identical or different substituents selected from the group consisting of
Preferably, one or two identical or different substituents selected from the group consisting of a chlorine atom, a bromine atom, a fluorine atom, a methyl group and an ethyl group are pyridylcarbonyl groups substituted by a pyridine ring.

In the present invention, “the thienylcarbonyl group substituted by _{1 to} 3 identical or different halogen atoms or C _{1 to} C ₆ alkyl groups” includes the above “halogen atom” and the above “C _{1 to} C 6 ₆ alkyl groups "is a thienylcarbonyl group having the same or different 1 to 3 substituents selected from the group consisting of
Preferably, one or two identical or different substituents selected from the group consisting of a chlorine atom, a bromine atom, a fluorine atom, a methyl group and an ethyl group are thienylcarbonyl groups substituted on a thiophene ring.

In the present invention, the "C ₂ -C ₇ alkyl (thiocarbonyl) group" is a thiocarbonyl group to which a linear or branched alkyl group having 1 to 6 carbon atoms is bonded.
Preferably, it is a thiocarbonyl group {C ₂ -C ₅ alkyl (thiocarbonyl) group} to which a linear or branched alkyl group having 1 to 4 carbon atoms is bonded, and more preferably, methyl (thiocarbonyl) Or an ethyl (thiocarbonyl) group.

In the present invention, "the same or different
1 to 5 halogen atoms or 1 C₁~ C₆Alkoki
Si group, C₁~ C₆By an alkylthio or cyano group
Replaced C_Two~ C₇"Alkoxycarbonyl group"
1 to 5 different "halogen atoms"
Or one of the above "C₁~ C₆Alkoxy group "and the aforementioned" C ₁
~ C₆Before alkylthio group or cyano group is bonded
Note "C_Two~ C₇Alkoxycarbonyl group ''
Are the same or different 1 to 5 fluorine atoms
Or a chlorine atom or one of the above "C₁~ C_FourAlkoxy
Group) and the aforementioned "C₁~ C_FourAlkylthio group "or cyano
The above “C” to which the group is bonded_Two~ C_FiveAlkoxycarbonyl group "
And more preferably the same or different 1 to 5
Fluorine or chlorine atoms or one of the above “C₁
~ C_TwoThe aforementioned “C” to which an “alkoxy group” is bonded. _Two~ C_FiveArco
Xycarbonyl group '', and even more preferably,
Or one to three different chlorine atoms or one methoxide
The above-mentioned “C_Two~ C_FiveAlkoxycarbonyl
Group ", and particularly preferably, 1-chloroethoxycarbo.
Nil, 2-chloroethoxycarbonyl, 2,2,2-to
Lichloroethoxycarbonyl, 2,2,2-trifluoro
Roethoxycarbonyl, 2-methoxyethoxycarboni
Or a 2-ethoxyethoxycarbonyl group.

In the present invention, "C_Three~ C₇Alkenylo
The “xycarbonyl group” refers to the above-mentioned “C _Two~ C₆Alkenylo
A carbonyl group to which an `` xy group '' is bonded,
Carboxy to which an alkenyloxy group having a prime number of 2 to 4 is bonded
Nyl group (C_Three~ C_FiveAlkenyloxy group)
Suitably, an alkenyloxy group having 2 or 3 carbon atoms is bonded.
Carbonyl group (C_Three~ C_FourAlkenyloxy group)
And even more preferably allyloxycarbonyl or butyl.
It is a phenyloxycarbonyl group.

In the present invention, “1 to 5 identical or different phenoxycarbonyl groups substituted by _{1 to} 5 halogen atoms or C _{1 to} C ₆ alkyl groups” means _{1 to} 5 identical or different halogen atoms. a phenoxycarbonyl group atoms "or the" C ₁ -C ₆ alkyl group "is bonded to the benzene ring, preferably, 1 to 3 identical or different fluorine atoms, chlorine atom, a methyl group or an ethyl group It is a substituted phenoxycarbonyl group.

In the present invention, the "C ₂ -C ₇ (alkylthio) carbonyl group" is a carbonyl group having an alkylthio group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. A carbonyl group {C ₂ -C ₅ (alkylthio) carbonyl group} to which an alkylthio group is bonded,
More preferably, it is a (methylthio) carbonyl or (ethylthio) carbonyl group.

In the present invention, the “C ₂ -C ₇ alkyldithiocarbonyl group” is a thiocarbonyl group to which an alkylthio group having 1 to 6 carbon atoms is bonded.
A thiocarbonyl group having 1 to 4 carbon atoms and an alkylthio group bonded thereto (C ₂ -C ₅ alkyldithiocarbonyl), more preferably a methyldithiocarbonyl or ethyldithiocarbonyl group.

In the present invention, the “C ₃ -C ₈ alkylcarbonylcarbonyl group” is a carbonyl group to which the above “C ₂ -C ₇ alkylcarbonyl group” is bonded, and preferably has 2 to 5 carbon atoms. Is a carbonyl group (C ₃ -C ₆ alkylcarbonylcarbonyl group) to which the alkylcarbonyl group is bonded.

In the present invention, the “C ₃ -C ₈ alkoxycarbonylcarbonyl group” is a carbonyl group to which the above “C ₂ -C ₇ alkoxycarbonyl group” is bonded, and preferably has 2 to 5 carbon atoms. (C ₃ -C ₆ alkoxycarbonyl group), more preferably a carbonyl group (C ₃ -C ₄ alkoxycarbonyl) having an alkoxycarbonyl group having 2 or 3 carbon atoms bonded thereto. And even more preferably a carbonyl group to which an ethylcarbonyl group is bonded.

In the present invention, “(C ₂ -C ₇ alkoxycarbonyl) C ₁ -C ₆ alkyl group” refers to the aforementioned “C ₂ -C ₆ alkoxycarbonyl”.
Wherein the C ₇ alkoxycarbonyl "is bound one" C ₁ ~
A C ₆ alkyl group ", preferably a said" C ₂ -C ₅ alkoxycarbonyl "is the bound one" C ₁ -C ₄ alkyl group ", more preferably, methoxycarbonyl or ethoxycarbonyl A methyl or ethyl group to which a group is attached.

In the present invention, “one or two identical or different C ₁ -C ₆ alkyl groups, C ₂ -C ₇ alkoxycarbonyl groups, (C ₂ -C ₇ alkoxycarbonyl) C ₁
An aminocarbonyl group substituted by a C ₆ alkyl group or one phenyl group (the phenyl group may be substituted by the same or different 1 to 5 halogen atoms) ”. One or two of the above “C ₁ -C ₆ alkyl groups”, the “C ₂ -C ₇ alkoxycarbonyl groups”, the “(C ₂ -C ₇ alkoxycarbonyl) C ₁ -C ₆ alkyl groups” or the same Or an aminocarbonyl group to which one phenyl group which may be substituted by 1 to 5 different halogen atoms is bonded, preferably one or two of the same or different “C ₁
-C ₄ alkyl group ", the" C ₂ -C ₅ alkoxycarbonyl group ", the" C ₂ -C ₅ alkoxycarbonyl wherein the carbonyl group "is bonded to one" C ₁ -C ₄ alkyl group "or the same or different It is an aminocarbonyl group to which one phenyl group which may be substituted by 1 to 5 fluorine atoms, chlorine atoms or bromine atoms is bonded, more preferably one or two of the same or different “C ₁ ~C ₂ alkyl group "
Alternatively, it is an aminocarbonyl group to which one phenyl group which may be substituted by one fluorine atom or chlorine atom is bonded, and still more preferably one methyl group, phenyl group or monochlorophenyl group.

In the present invention, “an aminothiocarbonyl group substituted by one or two identical or different C ₁ -C ₆ alkyl groups” refers to one or two of the above “C ₁ -C ₆ alkyl groups” Is preferably an aminothiocarbonyl group having one or two of the above-mentioned “C ₁ -C ₄ alkyl groups” bonded thereto, and more preferably the above-mentioned “C ₁ -C ₂ alkyl group”. It is an aminothiocarbonyl group to which one “alkyl group” is bonded.

In the present invention, “furanylcarbonyl group substituted by 1 to 3 identical or different halogen atoms” refers to furanylcarbonyl group having 1 to 3 identical or different “halogen atoms” bonded thereto. And preferably a furanylcarbonyl group having 1 to 3 identical or different chlorine, bromine or fluorine atoms bonded thereto.

In the present invention, the term “the same or different C ₁ -C ₆ alkyl group or a pyrazolylcarbonyl group substituted by a halogen atom” means the same or different “C ₁ -C ₆ alkyl group”. A pyrazolylcarbonyl group in which one or two "halogen atoms" are bonded, and preferably the same or different "C
₁ -C ₄ alkyl group ", a chlorine atom, a bromine atom or a fluorine atom is one or two bonded pyrazolyl group.

In the present invention, the "C ₁ -C ₆ alkylsulfonyl group" is a sulfonyl group having a chain alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. A sulfonyl group having a chain alkyl group bonded thereto,
More preferably, it is a sulfonyl group to which a chain alkyl group having 1 or 2 carbon atoms is bonded.

In the present invention, “the same or different 1 to 5 C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group or phenylsulfonyl group substituted by a halogen atom” refers to the aforementioned “C ₁ -C ₆ alkyl group ", the" C ₁
A phenylsulfonyl group in which 1 to 5 substituents selected from the group consisting of a “C ₆ alkoxy group” and the “halogen atom” are bonded to a benzene ring, preferably the “C ₁ -C ₄ alkyl” A phenylsulfonyl group in which 1 to 5 substituents selected from the group consisting of a fluorine atom, a chlorine atom and a bromine atom are bonded to a benzene ring, more preferably 1 to 3 identical or different Is a phenylsulfonyl group in which a methyl group, an ethyl group, a fluorine atom or a bromine atom is bonded to a benzene ring, and still more preferably a phenylsulfonyl group in which one methyl or ethyl group is bonded.

In the present invention, “an aminosulfonyl group substituted by the same or different one or two C ₁ -C ₆ alkyl groups” is the same or different 1 or 2
A number of the aminosulfonyl group "C ₁ -C ₆ alkyl group" is bonded, preferably, identical or different one or two of the aminosulfonyl group "C ₁ -C ₄ alkyl group" is bonded And more preferably an aminosulfonyl group to which _{one of the} “C ₁ -C ₂ alkyl groups” is bonded.

[0054] In the present invention, a "(C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group", said the "C ₁ -C ₆ alkoxy group" is bonded one "C ₁ -C ₆ alkyl a group ", preferably, the" C ₁ -C ₄ wherein the alkoxy group "is bonded to one" C ₁ -C ₄ alkyl group "{(C ₁ -C ₄ alkoxy) C ₁ -C ₄ alkyl group ｝.

In the present invention, "an amino group substituted by one or two identical or different C ₁ -C ₆ alkyl groups or (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl groups"
Means the “C ₁ -C ₆ alkyl group” or the “(C ₁ -C ₆ alkyl group)”.
An amino group in which one or two C ₆ -alkoxy) C ₁ -C ₆ alkyl groups are bonded, and preferably the above-mentioned “C ₁ -C ₄ alkyl group” or the above “(C ₁ -C ₄ alkoxy) C ₁ -C is ₄ alkyl group "is 1 or 2 bound amino groups, more preferably, which is the" C ₁ -C ₂ alkyl group "amino group in which one is bound.

In the present invention, "the same or different
One or two C₁~ C₆An alkyl group (the alkyl group is
By 1 to 5 identical or different halogen atoms
It may be substituted. ), Phenyl group (the phenyl group
Is C₁~ C₆Alkyl group, halogen atom and C₁~ C₆A
1 to 5 identical members selected from the group consisting of
Or different substituents. ),
Halogen atom, C_Two~ C₇Alkoxycarbonyl group,
A nonoxycarbonyl group or an amino group (the amino group
One or two different Cs₁~ C₆Alkyl group
Is (C₁~ C₆Alkoxy) C₁~ C₆By alkyl group
May be replaced. A methylidene group substituted by a)
Means “C₁~ C₆Alkyl group "and" the same
Is substituted by 1 to 5 different halogen atoms
C₁~ C₆Alkyl group ", phenyl group," halogen atom,
C₁~ C₆Alkyl group and C₁~ C₆Consists of an alkoxy group
1 to 5 identical or different substitutions selected from the group
A phenyl group substituted by a group ''
"C"_Two~ C₇Alkoxycarbonyl group ",
A nonoxycarbonyl group, an amino group and the above "1 or 2
Same or different C₁~ C₆Alkyl group or (C₁~
C₆Alkoxy) C₁~ C₆Substituted by an alkyl group
Same or different selected from the group consisting of "amino group"
A methylidene group having one or two substituents bonded thereto,
Preferably, the "C₁~ C_FourAlkyl group ","
Is represented by one to five different fluorine or chlorine atoms
Replaced C₁~ C₆Alkyl group ", phenyl group," C₁
~ C_FourAlkyl group, fluorine atom, chlorine atom and C₁~ C_Four
Same or different selected from the group consisting of alkoxy groups
Phenyl substituted by only 1 to 5 substituents
Group ", fluorine atom, chlorine atom, bromine atom," C_Two~ C_FiveA
Alkoxycarbonyl group '', phenoxycarbonyl group,
Amino group and one or two identical or different C
₁~ C_FourAlkyl group or (C ₁~ C_FourAlkoxy) C₁~ C_Four
Amino group substituted by an alkyl group "
One or two selected identical or different substituents are linked.
Combined methylidene groups, more preferably C₁~ C_TwoA
Alkyl group, C_Two~ C_ThreeAn alkoxycarbonyl group and “1 or
Is two identical or different C₁~ C_TwoBy alkyl group
Selected from the group consisting of
Or methylide to which one or two different substituents are bonded
And even more preferably one or the same or different
Represents two methyl, ethoxycarbonyl or monoethyl groups
A methylidene group substituted by a phenylamino group.

In the present invention, “C ₂ -C ₇ alkylcarbonylthio” refers to, for example, methylcarbonylthio,
Ethylcarbonylthio, isopropylcarbonylthio,
A straight-chain or branched alkylcarbonylthio group having 1 to 6 carbon atoms such as propylcarbonylthio, butylcarbonylthio, pentylcarbonylthio, and hexylcarbonylthio, and preferably a straight-chain having 1 to 4 carbon atoms. Or a branched alkylcarbonylthio group, more preferably an alkylcarbonylthio group having 1 or 2 carbon atoms.

In the present invention, “C ₁ -C ₆ alkylsulfonyloxy group” includes, for example, methylsulfonyloxy, ethylsulfonyloxy, isopropylsulfonyloxy, propylsulfonyloxy, butylsulfonyloxy, pentylsulfonyloxy, hexylsulfonyloxy And a linear or branched alkylsulfonyloxy group having 1 to 6 carbon atoms such as
And 4 to 4 linear or branched alkylsulfonyloxy groups, more preferably a methylsulfonyloxy or ethylsulfonyloxy group.

In the present invention, “C ₆ -C ₁₀ arylsulfonyloxy group” means, for example, phenylsulfonyloxy, 1-naphthylsulfonyloxy, 2-naphthylsulfonyloxy, 1-anthranilic sulfonyloxy, 2-anthane An arylsulfonyloxy group having 6 to 10 carbon atoms such as tranylsulfonyloxy, preferably an arylsulfonyloxy group having 6 to 8 carbon atoms, more preferably a phenylsulfonyloxy group It is.

In the present invention, "halogen atom or C₁
~ C₆C substituted by an alkyl group ₆~ C_TenAryls
“Ruphonyloxy group” means the above “halogen atom” and
Note "C₁~ C₆Selected from the group consisting of "alkyl groups"
Alternatively, the above-mentioned “C” having 1 to 5 different substituents bonded thereto
₆~ C_TenArylsulfonyloxy group '', preferably
Represents a fluorine atom, a chlorine atom, a bromine atom and the aforementioned “C₁~
C_FourThe same or selected from the group consisting of
The aforementioned “C” in which 1 to 5 different substituents are bonded. ₆~ C
_TenArylsulfonyloxy group '', more preferably
Represents a fluorine atom, a chlorine atom, a bromine atom and the aforementioned “C₁~
C_TwoThe same or selected from the group consisting of
6 to 8 carbon atoms having 1 to 3 different substituents bonded
Arylsulfonyloxy groups, even more preferred
Contains from chlorine, bromine, methyl and ethyl groups
One or two identical or different members selected from the group consisting of
It is a phenylsulfonyloxy group to which a substituent is bonded.

In the present invention, “(C ₁ -C ₆ alkyl)
The “aminocarbonyl group” is an aminocarbonyl group in which one or two of the above “C ₁ -C ₆ alkyl groups” are substituted,
Preferably, the “C ₁ -C ₄ alkyl group” is an aminocarbonyl group substituted with one, more preferably an aminocarbonyl group substituted with one methyl group or ethyl group.

In the present invention, “C ₁ -C ₆ substituted by 1 to 5 identical or different halogen atoms”
The alkyl) aminocarbonyl group "is a the" same or different 1 to 5 C ₁ is substituted by a halogen atom -C ₆ alkyl group "is 1 or 2 substituted aminocarbonyl group, preferably a Same or different one
An aminocarbonyl group substituted by _{one of} the above-mentioned “C ₁ -C ₄ alkyl groups” substituted with 1 to 3 fluorine atoms, chlorine atoms or bromine atoms, more preferably a trifluoromethyl group or a trifluoroethyl group Is a substituted aminocarbonyl group.

In the present invention, “alkali metal” means
For example, lithium, potassium and sodium can be mentioned, and preferably potassium or sodium.

In the present invention, the formula C (R ² ) (R ³ ) SO
_n a group represented by R ¹ and a formula C {= NN (R ⁵ ) (R ⁶ )}
The position at which the group represented by the formula C (R ² ) (R ³ ) SO _n R ¹ is bonded to the heterocycle to which the group represented by C ₆ H _(5-m) X _m is bonded is preferably Position 2 or position 3, more preferably 2
And C ｛= NN (R ⁵ ) (R ⁶ ) C ₆ H _{(5- m)}
The position where the group represented by X _m is bonded is preferably at the 4- or 5-position, more preferably at the 5-position.

The compound (I) of the present invention may be, for example, a hydrogen halide such as hydrogen chloride or hydrogen bromide; another inorganic acid such as sulfuric acid, nitric acid or phosphoric acid;
Organic sulfonic acids such as toluenesulfonic acid; or other organic acids such as trifluoroacetic acid and oxalic acid (preferably hydrogen halide or organic sulfonic acids, more preferably hydrogen chloride or methanesulfonic acid Can be converted to a salt. These salts
As long as it can be used as a pesticide, it is included in the present invention.

The hydrate of the compound of the present invention is also included in the present invention.

The compounds of the present invention include optical isomers,
Sex and tautomers may exist, in which case
The present invention relates to any one of the isomers and
It also includes mixtures of proportions. (A) In the general formula (I), R¹Is preferably
Is C₁~ C_FourAn alkyl group (the alkyl group may be the same or different
Or 1 to 5 different fluorine or chlorine atoms
May be substituted. ) Or C_Two~ C_FourWith an alkenyl group
Yes, more preferably C₁~ C_ThreeAlkyl group, most
Preferably, it is an ethyl group. (B) In the general formula (I), n is preferably
It is 0 or 2, more preferably 0. (C) In the general formula (I), R^TwoAnd R^ThreeIs good
Suitably, same or different, hydrogen atom or C₁~ C_Four
Alkyl groups, and more preferably, both are hydrogen atoms.
You. (D) In the general formula (I), A is preferably
Oxygen atom, sulfur atom or formula NR⁶The basic formula represented by
Medium, R⁶Is a hydrogen atom or C₁~ C_FourRepresents an alkyl group
You. ｝, More preferably an oxygen atom or a sulfur atom
And most preferably a sulfur atom. (E) In the general formula (I), Y is preferably
Fluorine atom, chlorine atom, bromine atom or C₁~ C_FourAlkyl
And when p is 2, a plurality of Y are the same
Or may be different, p is preferably 0. (F) In the general formula (I), R^FourAnd R^FiveIs good
Suitably, same or different, hydrogen atom, C₁~ C_FourA
Alkyl group (the alkyl group is the same or different
From 5 to 5 fluorine or chlorine atoms or 1 C₁
~ C_FourAlkoxy group, C₁~ C_FourAlkylthio group, C_Two~ C
_FiveAlkoxycarbonyl group, pyridyloxy group, cyano
It may be substituted by a group or a hydroxyl group. ), C_Two
~ C_FourAlkenyl group, C_Two~ C_FourAlkynyl group, C_Two~ C_Ten
Alkylcarbonyl group (the alkylcarbonyl group is
1 to 5 same or different fluorine atoms or
Chlorine atom or one C₁~ C_FourAlkoxy group, phenoxy
Group, C₁~ C_FourAlkylthio group, phenylthio group or
It may be substituted by a cyano group. ), C_Three~ C_FiveAl
Kenylcarbonyl group (the alkenylcarbonyl group is
1 to 5 same or different fluorine atoms or
Substituted by chlorine atom or one phenyl group
No. ), C_Three~ C_FiveAlkynylcarbonyl group, benzoyl
Groups (the benzoyl groups may be the same or different
5 fluorine atoms, chlorine atoms or bromine atoms or C₁
~ C_FourIt may be substituted by an alkyl group. ), Pil
A zircarbonyl group, a thienylcarbonyl group, C_Two~ C_FiveA
Alkyl (thiocarbonyl) group {-C (= S)-},
Nyl (thiocarbonyl) group {-C (= S)-}, C_Two~
C_FiveAlkoxycarbonyl group (the alkoxycarbon
The same or different 1 to 5 fluorine atoms
Or a chlorine atom or one C₁~ C_FourAlkoxy group, C
₁~ C_FourSubstituted by an alkylthio group or a cyano group
May be. ), C_Three~ C _FiveAlkenyloxycarbonyl
Group, phenoxycarbonyl group, C_Two~ C_Five(Alkyl
E) carbonyl group {-SC (= O)-}, (phenyl
Thio) carbonyl group, C_Two~ C_FiveAlkyl dithiocarboni
Group, phenyldithiocarbonyl group, C_Three~ C₆Alkyl
Carbonylcarbonyl group, phenylcarbonylcarboni
Group, C_Three~ C₆Alkoxycarbonylcarbonyl group,
Phenoxycarbonylcarbonyl group, aminocarbonyl group
{The aminocarbonyl groups are the same or different.
Or two C₁~ C_FourAlkyl group or one phenyl group
(1 to 5 identical or different phenyl groups
Is replaced by a fluorine, chlorine, or bromine atom
You may be. ) May be substituted. ｝, Ami
A nothiocarbonyl group (the aminothiocarbonyl group is
1 or 2 identical or different C₁~ C_FourAlkyl group
May be substituted by ), C₁~ C_FourAlkylsul
Phonyl group, phenylsulfonyl group (
Nyl group is the same or different 1 to 5 C₁~ C_Four
By alkyl group, fluorine atom, chlorine atom or bromine atom
It may be substituted. ) Or aminosulfonyl group (
The aminosulfonyl group may be the same or different 1 or 2
C₁~ C_FourIt may be substituted by an alkyl group. )
Or R^FourAnd R^FiveTogether, methylidene
Group—the methylidene groups may be the same or different
Two C₁~ C_FourAn alkyl group (the alkyl group is the same
Or 1 to 5 different fluorine or chlorine atoms
It may be more substituted. ), A phenyl group (the phenyl
The radical is C₁~ C_FourAlkyl group, halogen atom and C₁~
C_FourIdentical or selected from the group consisting of alkoxy groups
Substituted with 1 to 5 different substituents.
No. ), C_Two~ C_FiveAlkoxycarbonyl group, phenoxy
Carbonyl group or amino group (the same amino group
Or one or two different C₁~ C_FourBy alkyl group
May be replaced. ) May be substituted. }so
And, more preferably, the same or different
Child, C₁~ C_TwoAn alkyl group (the alkyl group has one C
₁~ C_TwoAlkoxy group, C₁~ C_TwoAlkylthio group or C_Two
~ C_ThreeMay be substituted by an alkoxycarbonyl group
No. ), C_Two~ C_TenAlkylcarbonyl group (the alkyl
1 to 3 identical or different
Fluorine or chlorine atom or one C₁~ C_TwoArco
Xy group, phenoxy group, C₁~ C_TwoAlkylthio group
May be substituted by a cyano group. ), C _Three~ C_FourA
Lucenylcarbonyl group, benzoyl group (the benzoyl
The groups are the same or different and have 1 to 5 fluorine atoms.
Alternatively, it may be substituted by a chlorine atom. ), Pirizi
Carbonyl group, thienylcarbonyl group, C_Two~ C_FiveAl
A oxycarbonyl group (the alkoxycarbonyl group is
1 to 5 same or different fluorine atoms or
Chlorine atom or one C₁~ C_TwoSubstituted by an alkoxy group
You may be. ), C_Three~ C_FourAlkenyloxycarboni
Group, C_Three~ C_FourAlkoxycarbonylcarbonyl group,
Aminocarbonyl group--the aminocarbonyl group is the same
Or one or two different C₁~ C_TwoAlkyl group or 1
Phenyl groups (the phenyl group is one fluorine atom
Alternatively, it may be substituted by a chlorine atom. By)
It may be substituted.ア ミ ノ, aminothiocarbonyl group (this
The aminothiocarbonyl group has one C₁~ C_TwoAlkyl
May be substituted by a group. ) Or C₁~ C_TwoAlkyl
Represents a sulfonyl group;^FourAnd R^FiveTogether
The methylidene group is the same or
One or two different C₁~ C_TwoAlkyl group, C_Two~ C_ThreeA
Alkoxycarbonyl group or amino group (the amino group is
1 or 2 identical or different C₁~ C_TwoAlkyl group
May be substituted by )
No. ｝, And even more preferably the same or different
A hydrogen atom, a methyl group (the methyl group is
Substituted by an xy or ethoxycarbonyl group
Good. ), C_Two~ C_TenAlkylcarbonyl group (the
1 to 3 identical or different killcarbonyl groups
A chlorine atom or one methoxy, phenoxy,
Substituted by a luthio or cyano group
No. ), Propenylcarbonyl group, benzoyl group (the
The benzoyl group is the same or different 1 to 5 salts
It may be substituted by an element atom. ), Pyridylcarbo
Nyl group, thienylcarbonyl group, C_Two~ C_FiveAlkoxyka
Rubonyl group (the alkoxycarbonyl group may be the same or different
1 to 3 different chlorine atoms or 1 methoxy
May be substituted by a group. ), Allyloxycarbo
Nyl group, butenyloxycarbonyl group, ethoxycarbo
Nilcarbonyl group, aminocarbonyl group
A rubonyl group is a methyl or phenyl group (the
The phenyl group may be substituted by one chlorine atom.
No. ) May be substituted. ｝, Monomethylami
A nothiocarbonyl group or a methanesulfonyl group;
Is R^FourAnd R^FiveTogether form a methylidene group
Tylidene group is one or two methyl groups which are the same or different.
Group, ethoxycarbonyl group or monoethylamino group
It may be more substituted. ｝. (G) In the general formula (I), X is preferably
A chlorine atom, a bromine atom or a fluorine atom, and m is
And more preferably X is a chlorine atom, a bromine atom or
Is a fluorine atom, m is 1, and the substitution position is
In position 4, and even more preferably, X is a chlorine atom
Where m is 1 and the substitution position is position 4. (1) In the general formula (I), (1)
a) R¹Is C₁~ C_FourAlkyl group (the alkyl group
Is the same or different 1 to 5 fluorine atoms or
It may be substituted by a chlorine atom. ) Or C _Two~ C_FourA
(1b) n is 0, 1 or 2
R, (1c) R^TwoAnd R^ThreeAre the same or different,
Hydrogen atom or C₁~ C_FourAn alkyl group, and (1d) A
Is an oxygen atom, a sulfur atom or a formula NR⁶Group represented by
中 where R⁶Is a hydrogen atom or C₁~ C_FourRepresents an alkyl group
You. ｝, (1e) p is 0, and (1f)
R^FourAnd R^FiveAre the same or different and are each a hydrogen atom, C₁
~ C_FourAn alkyl group (the alkyl groups may be the same or different
1 to 5 fluorine or chlorine atoms or 1
C₁~ C_FourAlkoxy group, C₁~ C_FourAlkylthio group,
C_Two~ C_FiveAlkoxycarbonyl group, pyridyloxy group,
Substituted by a cyano group or a hydroxyl group
No. ), C_Two~ C_FourAlkenyl group, C_Two~ C_FourAlkynyl
Group, C_Two~ C_TenAlkylcarbonyl group (the alkyl
A rubonyl group is the same or different and has 1 to 5 fluorine atoms.
Elementary atom or chlorine atom or one C₁~ C_FourAlkoxy
Group, phenoxy group, C₁~ C_FourAlkylthio group, phenyl
Substituted by a thio or cyano group
No. ), C_Three~ C_FiveAlkenylcarbonyl group (the
1 to 5 identical or different carbonyl groups
To a fluorine or chlorine atom or one phenyl group
It may be more substituted. ), C_Three~ C_FiveAlkynylcar
Bonyl group, benzoyl group (the same benzoyl group
Or 1 to 5 different fluorine or chlorine atoms
Or bromine atom or C₁~ C_FourSubstituted by an alkyl group
May be. ), Pyridylcarbonyl group, thienylcarbo
Nyl group, C_Two~ C_FiveAlkyl (thiocarbonyl) group ｛-C
(= S)-{, phenyl (thiocarbonyl) group} -C
(= S)-｝, C_Two~ C_FiveAlkoxycarbonyl group (the
The alkoxycarbonyl groups may be the same or different.
Up to 5 fluorine or chlorine atoms or 1 C₁~
C_FourAlkoxy group, C₁~ C_FourAlkylthio group or
It may be substituted by an ano group. ), C_Three~ C_FiveArche
Nyloxycarbonyl group, phenoxycarbonyl group, C
_Two~ C_Five(Alkylthio) carbonyl group ｛-SC (=
O)-｝, (phenylthio) carbonyl group, C_Two~ C_FiveA
Ruquildithiocarbonyl group, phenyldithiocarbonyl
Group, C_Three~ C₆Alkylcarbonylcarbonyl group, phenyl
Carbonyl group, C_Three~ C₆Alkoxycarbo
Nilcarbonyl group, phenoxycarbonylcarbonyl
Group, aminocarbonyl group ｛The aminocarbonyl group is
1 or 2 identical or different C₁~ C_FourAlkyl group
Or one phenyl group (the phenyl group may be the same or different
Represents one to five different fluorine, chlorine, or
It may be substituted by a bromine atom. ) Is replaced by
May be. ｝, Aminothiocarbonyl group (the amino
One or two thiocarbonyl groups may be the same or different
C₁~ C_FourIt may be substituted by an alkyl group. ),
C₁~ C_FourAlkylsulfonyl group, phenylsulfonyl group
(The phenylsulfonyl groups may be the same or different
1 to 5 C₁~ C_FourAlkyl group, fluorine atom, chlorine source
And it may be substituted by a hydrogen atom or a bromine atom. ) Or Ami
Nosulfonyl group (the same aminosulfonyl group
Or one or two different C₁~ C_FourBy alkyl group
May be replaced. ) Or R^FourAnd R^FiveTogether
And the methylidene group is the same
Or one or two different C₁~ C_FourAlkyl group
The alkyl group is the same or different from 1 to 5 fluorines.
It may be substituted by an elemental atom or a chlorine atom. ),
Phenyl group (the phenyl group is₁~ C_FourAlkyl group, ha
Logen atom and C₁~ C_FourSelect from the group consisting of alkoxy groups
By the same or different 1 to 5 substituents
It may be substituted. ), C_Two~ C_FiveAlkoxycarboni
Group, phenoxycarbonyl group or amino group (the amino group
Is one or two identical or different C₁~ C_FourA
It may be substituted by a alkyl group. ) Is replaced by
May be. ｝ And (1 g) X represents a chlorine atom,
An element atom or a fluorine atom, and m is 1.
(2) More preferably, (2a) R¹Is C₁~ C_ThreeA
(2b) n is 0 or 2,
(2c) R^TwoAnd R^ThreeAre both hydrogen atoms, and (2
d) A is an oxygen atom or a sulfur atom, and (2e)
p is 0 and (2f) R^FourAnd R^FiveAre the same young
Is different from a hydrogen atom, C₁~ C_TwoAlkyl group
The kill group is one C₁~ C_TwoAlkoxy group, C₁~ C_TwoAl
Kirthio group or C_Two~ C_ThreeBy an alkoxycarbonyl group
It may be substituted. ), C_Two~ C_{1 0}Alkyl carboni
(The alkylcarbonyl group may be the same or different
Only 1 to 3 fluorine or chlorine atoms or 1
C₁~ C_TwoAlkoxy group, phenoxy group, C₁~ C_TwoAl
Substituted by a quinthio group or a cyano group
No. ), C_Three~ C_FourAlkenylcarbonyl group, benzoyl
Groups (the benzoyl groups may be the same or different
Substituted by 5 fluorine or chlorine atoms
May be. ), Pyridylcarbonyl group, thienylcarbonyl
Group, C_Two~ C_FiveAlkoxycarbonyl group (the alkoxy
Cicarbonyl groups are the same or different and 1 to 5
Fluorine or chlorine atom or one C₁~ C_TwoArco
It may be substituted by a xy group. ), C_Three~ C_FourArche
Nyloxycarbonyl group, C_Three~ C_FourAlkoxycarboni
Carbonyl group, aminocarbonyl group
A bonyl group may be one or two identical or different C₁~
C_TwoAn alkyl group or one phenyl group (the phenyl group
Is substituted by one fluorine or chlorine atom
May be. ) May be substituted. },amino
A thiocarbonyl group (the aminothiocarbonyl group is 1
C₁~ C_TwoIt may be substituted by an alkyl group. )
Or C₁~ C_TwoRepresents an alkylsulfonyl group, or R^Four
And R^FiveTogether form a methylidene group
One or two identical or different C₁~ C_TwoA
Alkyl group, C_Two~ C_ThreeAlkoxycarbonyl group or amino
Group (the amino group is the same or different one or two
C₁~ C_TwoIt may be substituted by an alkyl group. )
It may be more substituted. And (2g) X is
A chlorine atom, a bromine atom or a fluorine atom, and m is 1
And the substitution position is position 4, (3)
Suitably, (3a) R¹Is an ethyl group, and (3b)
 n is 0, and (3c) R^TwoAnd R^ThreeAre together, water
A is a sulfur atom, (3d) A is a sulfur atom, and (3d)
e) p is 0 and (3f) R^FourAnd R^FiveAre the same
Or differently, a hydrogen atom, a methyl group (the methyl group
Is represented by one ethoxy group or ethoxycarbonyl group
It may be substituted. ), C_Two~ C_TenAlkyl carboni
(The alkylcarbonyl group may be the same or different
Only one to three chlorine atoms or one methoxy group,
Substituted by a nonoxy, methylthio or cyano group
You may be. ), Propenylcarbonyl group, benzoy
(The benzoyl group may be the same or different)
It may be substituted by up to 5 chlorine atoms. ), Pil
A zircarbonyl group, a thienylcarbonyl group, C_Two~ C_FiveA
Alkoxycarbonyl group (the alkoxycarbonyl group
Are the same or different 1 to 3 chlorine atoms or 1
Methoxy groups. ), Allyl
Oxycarbonyl group, butenyloxycarbonyl group, d
Toxicarbonylcarbonyl group, aminocarbonyl group
｛The aminocarbonyl group is one methyl group or
Nyl group (the phenyl group is substituted by one chlorine atom
May have been. ) May be substituted. ｝, Mo
Nomethylaminothiocarbonyl group or methanesulfonyl
Represents a group, or R^FourAnd R^FiveTogether,
The methylidene groups may be the same or different.
Represents two methyl, ethoxycarbonyl or monoethyl groups
It may be substituted by a ruamino group. ｝ And (3
g) X is a chlorine atom, m is 1 and
The replacement position is fourth.

In the above general formula (II), R^TwoAnd R^Three
Are preferably the same or different and each represents a hydrogen atom or C
₁~ C_FourAlkyl groups, more preferably, both
And A is preferably an oxygen atom, a sulfur atom or a formula
NR⁶In the formula, R represents⁶Is a hydrogen atom or C₁
~ C_FourShows an alkyl group. ｝, And more preferably an acid
An elemental atom or a sulfur atom, most preferably a sulfur atom
And Y is preferably a fluorine atom, a chlorine atom, a bromine atom.
Child or C₁~ C_FourAn alkyl group, and when p is 2,
A plurality of Y may be the same or different, and p is
Preferably, it is 0, and X is preferably chlorine atom, bromine
An atom or a fluorine atom, and m is 1,
Preferably, X is a chlorine, bromine or fluorine atom
And m is 1 and the substitution position is position 4,
More preferably, X is a chlorine atom and m is 1.
And the substitution position is position 4,⁷Is preferably
Formula SO_nR¹[Wherein, R¹Is C₁~ C_FourAlkyl group
The alkyl group is the same or different from 1 to 5 fluorines.
It may be substituted by an elemental atom or a chlorine atom. ) Or
C_Two~ C_FourRepresents an alkenyl group, and n represents 0, 1 or 2
You. And more preferably a group represented by the formula SO_nR¹
[Wherein, R¹Is C₁~ C _ThreeRepresents an alkyl group, and n is 0
Or 2. A group represented by the formula:
Is an ethylthio group.

In the above general formula (III), R^Twoas well as
R^ThreeAre preferably the same or different and are each a hydrogen atom or
Is C₁~ C_FourAlkyl groups, more preferably water
A is preferably an oxygen atom, a sulfur atom or
Is the formula NR⁶In the formula, R represents⁶Is a hydrogen atom or
C₁~ C_FourShows an alkyl group. ｝, And more preferably,
An oxygen atom or a sulfur atom, most preferably a sulfur atom
And Y is preferably a fluorine atom, a chlorine atom, a bromine
Atom or C₁~ C_FourAn alkyl group, and p is 2
And a plurality of Y may be the same or different, and p
Is preferably 0, and when p is 2, a plurality of Y
May be the same or different, and R^FourAnd R^FiveIs
Preferably, same or different, hydrogen atom, C₁~ C_Four
An alkyl group (the alkyl groups may be the same or different
1 to 5 fluorine or chlorine atoms or 1 C
₁~ C_FourAlkoxy group, C₁~ C_FourAlkylthio group, C_Two~
C_FiveAlkoxycarbonyl group, pyridyloxy group, shea
And may be substituted by a hydroxyl group or a hydroxyl group. ), C
_Two~ C_FourAlkenyl group, C_Two~ C_FourAlkynyl group, C_Two~ C
_TenAlkylcarbonyl group (the alkylcarbonyl group
Are the same or different 1 to 5 fluorine atoms
Is a chlorine atom or one C₁~ C_FourAlkoxy group, pheno
Xy group, C₁~ C_FourAlkylthio group, phenylthio group
Or may be substituted by a cyano group. ), C_Three~ C_Five
Alkenylcarbonyl group (the alkenylcarbonyl group
Are the same or different 1 to 5 fluorine atoms
Substituted by a chlorine atom or one phenyl group
May be. ), C_Three~ C_FiveAlkynylcarbonyl group, benzo
Yl group (the benzoyl group may be the same or different
From 5 to 5 fluorine, chlorine or bromine atoms or
C₁~ C_FourIt may be substituted by an alkyl group. ), Pi
Lysylcarbonyl group, thienylcarbonyl group, C_Two~ C_Five
An alkyl (thiocarbonyl) group {-C (= S)-},
Phenyl (thiocarbonyl) group {-C (= S)-}, C_Two
~ C_FiveAn alkoxycarbonyl group (the alkoxycarbo group
Nyl group is the same or different 1 to 5 fluorine atoms.
Child or chlorine atom or one C₁~ C_FourAn alkoxy group,
C₁~ C_FourSubstituted by an alkylthio group or a cyano group
You may be. ), C_Three~ C_FiveAlkenyloxycarboni
Group, phenoxycarbonyl group, C_Two~ C_Five(Alkyl
E) carbonyl group {-SC (= O)-}, (phenyl
Thio) carbonyl group, C_Two~ C_FiveAlkyl dithiocarboni
Group, phenyldithiocarbonyl group, C_Three~ C₆Alkyl
Carbonylcarbonyl group, phenylcarbonylcarboni
Group, C_Three~ C₆Alkoxycarbonylcarbonyl group,
Phenoxycarbonylcarbonyl group, aminocarbonyl group
{The aminocarbonyl groups are the same or different.
Or two C₁~ C_FourAlkyl group or one phenyl group
(1 to 5 identical or different phenyl groups
Is replaced by a fluorine, chlorine, or bromine atom
You may be. ) May be substituted. ｝, Ami
A nothiocarbonyl group (the aminothiocarbonyl group is
1 or 2 identical or different C₁~ C_FourAlkyl group
May be substituted by ), C₁~ C_FourAlkylsul
Phonyl group, phenylsulfonyl group (
Nyl group is the same or different 1 to 5 C₁~ C_Four
By alkyl group, fluorine atom, chlorine atom or bromine atom
It may be substituted. ) Or aminosulfonyl group (
The aminosulfonyl group may be the same or different 1 or 2
C₁~ C_FourIt may be substituted by an alkyl group. )
Or R^FourAnd R^FiveTogether, methylidene
Group—the methylidene groups may be the same or different
Two C₁~ C_FourAn alkyl group (the alkyl group is the same
Or 1 to 5 different fluorine or chlorine atoms
It may be more substituted. ), A phenyl group (the phenyl
The radical is C₁~ C_FourAlkyl group, halogen atom and C₁~
C_FourIdentical or selected from the group consisting of alkoxy groups
Substituted with 1 to 5 different substituents.
No. ), C_Two~ C_FiveAlkoxycarbonyl group, phenoxy
Carbonyl group or amino group (the same amino group
Or one or two different C₁~ C_FourBy alkyl group
May be replaced. ) May be substituted. }so
And, more preferably, the same or different
Child, C₁~ C_TwoAn alkyl group (the alkyl group has one C
₁~ C_TwoAlkoxy group, C₁~ C_TwoAlkylthio group or C_Two
~ C_ThreeMay be substituted by an alkoxycarbonyl group
No. ), C_Two~ C_TenAlkylcarbonyl group (the alkyl
1 to 3 identical or different
Fluorine or chlorine atom or one C₁~ C_TwoArco
Xy group, phenoxy group, C₁~ C_TwoAlkylthio group
May be substituted by a cyano group. ), C _Three~ C_FourA
Lucenylcarbonyl group, benzoyl group (the benzoyl
The groups are the same or different and have 1 to 5 fluorine atoms.
Alternatively, it may be substituted by a chlorine atom. ), Pirizi
Carbonyl group, thienylcarbonyl group, C_Two~ C_FiveAl
A oxycarbonyl group (the alkoxycarbonyl group is
1 to 5 same or different fluorine atoms or
Chlorine atom or one C₁~ C_TwoSubstituted by an alkoxy group
You may be. ), C_Three~ C_FourAlkenyloxycarboni
Group, C_Three~ C_FourAlkoxycarbonylcarbonyl group,
Aminocarbonyl group--the aminocarbonyl group is the same
Or one or two different C₁~ C_TwoAlkyl group or 1
Phenyl groups (the phenyl group is one fluorine atom
Alternatively, it may be substituted by a chlorine atom. By)
It may be substituted.ア ミ ノ, aminothiocarbonyl group (this
The aminothiocarbonyl group has one C₁~ C_TwoAlkyl
May be substituted by a group. ) Or C₁~ C_TwoAlkyl
Represents a sulfonyl group;^FourAnd R^FiveTogether
The methylidene group is the same or
One or two different C₁~ C_TwoAlkyl group, C_Two~ C_ThreeA
Alkoxycarbonyl group or amino group (the amino group is
1 or 2 identical or different C₁~ C_TwoAlkyl group
May be substituted by )
No. ｝, And even more preferably the same or different
A hydrogen atom, a methyl group (the methyl group is
Substituted by an xy or ethoxycarbonyl group
Good. ), C_Two~ C_TenAlkylcarbonyl group (the
1 to 3 identical or different killcarbonyl groups
A chlorine atom or one methoxy, phenoxy,
Substituted by a luthio or cyano group
No. ), Propenylcarbonyl group, benzoyl group (the
The benzoyl group is the same or different 1 to 5 salts
It may be substituted by an element atom. ), Pyridylcarbo
Nyl group, thienylcarbonyl group, C_Two~ C_FiveAlkoxyka
Rubonyl group (the alkoxycarbonyl group may be the same or different
1 to 3 different chlorine atoms or 1 methoxy
May be substituted by a group. ), Allyloxycarbo
Nyl group, butenyloxycarbonyl group, ethoxycarbo
Nilcarbonyl group, aminocarbonyl group
A rubonyl group is a methyl or phenyl group (the
The phenyl group may be substituted by one chlorine atom.
No. ) May be substituted. ｝, Monomethylami
A nothiocarbonyl group or a methanesulfonyl group;
Is R^FourAnd R^FiveTogether form a methylidene group
Tylidene group is one or two methyl groups which are the same or different.
Group, ethoxycarbonyl group or monoethylamino group
It may be more substituted. Ｘ and X is preferably
A chlorine atom, a bromine atom or a fluorine atom, and m is
And more preferably X is a chlorine atom, a bromine atom or
Is a fluorine atom, m is 1, and the substitution position is
In position 4, and even more preferably, X is a chlorine atom
M is 1 and the substitution position is 4-position;^7a
Is preferably a halogen atom, C₁~ C₆Alkylsulfo
Nyloxy group or C₆~ C_TenArylsulfonylo
A xy group (the arylsulfonyloxy group is the same or different
Or 1 to 5 different C₁~ C₆By alkyl group
May be replaced. ) Or a mercapto group, C_Two~ C₇
Alkylcarbonylthio group or amidinosulfeni
Group.

Representative compounds of the present invention are shown in the following Tables 1 to 4, but the present invention is not limited to these compounds.

Hereinafter, “Me” is a methyl group, “Et” is an ethyl group, “Pr” is a propyl group, “iPr” is an isopropyl group, “Bu” is a butyl group, and “iBu” is isobutyl. A group, "sBu" is a sec-butyl group,
“TBu” represents a tert-butyl group and “neoC
₅ H ₁₁ "is a neopentyl group," cPr "cyclopropyl group," cBu "cyclobutyl group," cC ₅ H
₁₁ "a cyclopentyl group," cC ₆ H ₁₃ "is a cyclohexyl group," Ph "represents a phenyl group, a" Pyr "means pyridyl group, the" Thi "thienyl group" CO-5-
(1,4-Me ₂ -Pyza) ”is 1,4-dimethyl-
5-pyrazolylcarbonyl group, “Furo” represents a 2-furoyl group, “2-CO ₂ H—Bz” represents a 2-carboxylbenzoyl group, “trans” represents trans, and “c
“is” indicates cis, and “Phtl” indicates a phthaloyl group.

In the columns of Y _p , X _m and (R ⁴ , R ⁵ ), the number before the substituent indicates the substitution position of the substituent, and the subscript number after the substituent indicates the substitution position of the substituent. Shows the number of substituents on the group For example, 4-Cl is a chlorine atom substituted at the 4-position, 2-Pyr is a pyridyl group substituted at the 2-position,
4-Cl-Ph is a 4-chlorophenyl group.

In the following table, the presence of H in the column of Y _p indicates that p is 0.

[0074]

[Table 1]

[0075]

Embedded image ─────────────────────────────────── Compound number R ¹ n R ^Two R ^Three Y _p X (R ^Four , R ^Five ) ─────────────────────────────────── 1-1 Me 0 HHH Cl (H, H) 1- 2 Me 0 HHH Cl (H, COMe) 1-3 Me 0 HHH Cl (H, COEt) 1-4 Me 0 HHH Cl (H, COPr) 1-5 Me 0 HHH Cl (H, COiPr) 1-6 Me 0 HHH Cl (H, COBu) 1-7 Me 0 HHH Cl (H, COsBu) 1-8 Me 0 HHH Cl (H, COiBu) 1-9 Me 0 HHH Cl (H, COtBu) 1-10 Me 0 HHH Cl (H, COC _Five H ₁₁ ) 1-11 Me 0 HHH Cl (H, COneoC _Five H ₁₁ ) 1-12 Me 0 HHH Cl (H, COC ₆ H ₁₃ ) 1-13 Me 0 HHH Cl (H, COC ₇ H ₁₅ ) 1-14 Me 0 HHH Cl (H, COC ₈ H ₁₇ ) 1-15 Me 0 HHH Cl (H, COC ₉ H ₁₉ ) 1-16 Me 0 HHH Cl (H, COcPr) 1-17 Me 0 HHH Cl (H, COcBu) 1-18 Me 0 HHH Cl (H, COcC _Five H ₉ ) 1-19 Me 0 HHH Cl (H, COcC ₆ H ₁₁ ) 1-20 Me 0 HHH Cl (H, COCH = CH _Two ) 1-21 Me 0 HHH Cl (H, COCH = CHPh) 1-22 Me 0 HHH Cl (H, COCH = CHMe) 1-23 Me 0 HHH Cl (H, COCH = CHCl) 1-24 Me 0 HHH Cl (H, COC≡CH) 1-25 Me 0 HHH Cl (H, COC≡CMe) 1-26 Me 0 HHH Cl (H, COCH _Two CH = CH _Two ) 1-27 Me 0 HHH Cl (H, COCH _Two C≡CH) 1-28 Me 0 HHH Cl (H, COCH _Two F) 1-29 Me 0 HHH Cl (H, COCH _Two Cl) 1-30 Me 0 HHH Cl (H, COCH _Two Br) 1-31 Me 0 HHH Cl (H, COCH _Two OMe) 1-32 Me 0 HHH Cl (H, COCH _Two OEt) 1-33 Me 0 HHH Cl (H, COCH _Two OPh) 1-34 Me 0 HHH Cl (H, COCH _Two SMe) 1-35 Me 0 HHH Cl (H, COCH _Two SEt) 1-36 Me 0 HHH Cl (H, COCH _Two SPh) 1-37 Me 0 HHH Cl (H, COCH _Two CN) 1-38 Me 0 HHH Cl (H, CH _Two O (2-Pyr)) 1-39 Me 0 HHH Cl (H, CH _Two CO _Two Me) 1-40 Me 0 HHH Cl (H, CH _Two CO _Two Et) 1-41 Me 0 HHH Cl (H, COCH _Two CH _Two Cl) 1-42 Me 0 HHH Cl (H, COCH _Two CH _Two OMe) 1-43 Me 0 HHH Cl (H, COCH _Two CH _Two OEt) 1-44 Me 0 HHH Cl (H, COCH _Two CH _Two SMe) 1-45 Me 0 HHH Cl (H, COPh) 1-46 Me 0 HHH Cl (H, CO (4-Cl-Ph)) 1-47 Me 0 HHH Cl (H, CO (4-Me-Ph )) 1-48 Me 0 HHH Cl (H, CO (2-Pyr)) 1-49 Me 0 HHH Cl (H, CO (3-Pyr)) 1-50 Me 0 HHH Cl (H, CO (4- Pyr)) 1-51 Me 0 HHH Cl (H, CO (2-Thi)) 1-52 Me 0 HHH Cl (H, CO (3-Thi)) 1-53 Me 0 HHH Cl (H, C (S ) Me) 1-54 Me 0 HHH Cl (H, C (S) Et) 1-55 Me 0 HHH Cl (H, C (S) Ph) 1-56 Me 0 HHH Cl (H, CO _Two Me) 1-57 Me 1 HHH Cl (H, CO _Two Me) 1-58 Me 0 HHH Cl (H, CO _Two Et) 1-59 Me 1 HHH Cl (H, CO _Two Et) 1-60 Me 0 HHH Cl (H, CO _Two Pr) 1-61 Me 0 HHH Cl (H, CO _Two iPr) 1-62 Me 0 HHH Cl (H, CO _Two Bu) 1-63 Me 0 HHH Cl (H, CO _Two iBu) 1-64 Me 0 HHH Cl (H, CO _Two tBu) 1-65 Me 0 HHH Cl (H, CO _Two CH _Two CH = CH _Two ) 1-66 Me 0 HHH Cl (H, CO _Two CH _Two CH _Two OMe) 1-67 Me 0 HHH Cl (H, CO _Two CH _Two CH _Two OEt) 1-68 Me 0 HHH Cl (H, CO _Two CH _Two CH _Two Cl) 1-69 Me 0 HHH Cl (H, CO _Two CH _Two CH _Two SMe) 1-70 Me 0 HHH Cl (H, CO _Two CH _Two CH _Two CN) 1-71 Me 0 HHH Cl (H, CO _Two CH _Two Cl) 1-72 Me 0 HHH Cl (H, CO _Two CHClMe) 1-73 Me 0 HHH Cl (H, CO _Two CH _Two CCl _Three ) 1-74 Me 0 HHH Cl (H, CO _Two CH _Two CF _Three ) 1-75 Me 0 HHH Cl (H, CO _Two Ph) 1-76 Me 0 HHH Cl (H, COSMe) 1-77 Me 0 HHH Cl (H, COSEt) 1-78 Me 0 HHH Cl (H, COSPr) 1-79 Me 0 HHH Cl (H, CS _Two Me) 1-80 Me 0 HHH Cl (H, CS _Two Ph) 1-81 Me 0 HHH Cl (H, COCOMe) 1-82 Me 0 HHH Cl (H, COCOEt) 1-83 Me 0 HHH Cl (H, COCOPh) 1-84 Me 0 HHH Cl (H, COCO _Two Me) 1-85 Me 0 HHH Cl (H, COCO _Two Et) 1-86 Me 0 HHH Cl (H, COCO _Two Ph) 1-87 Me 0 HHH Cl (H, CONH _Two ) 1-88 Me 0 HHH Cl (H, CONMe) 1-89 Me 0 HHH Cl (H, CONMe _Two ) 1-90 Me 0 HHH Cl (H, CONEt _Two ) 1-91 Me 0 HHH Cl (H, CONH (4-Cl-Ph)) 1-92 Me 0 HHH Cl (H, SO _Two NH _Two ) 1-93 Me 0 HHH Cl (H, SO _Two NHMe) 1-94 Me 0 HHH Cl (H, SO _Two NMe _Two ) 1-95 Me 0 HHH Cl (H, SO _Two Me) 1-96 Me 0 HHH Cl (H, SO _Two Et) 1-97 Me 0 HHH Cl (H, SO _Two Ph) 1-98 Me 0 HHH Cl (H, SO _Two (4-Me-Ph) 1-99 Me 0 HHH Cl (= C (Me) NHMe) 1-100 Me 0 HHH Cl (= CHCO _Two Me) 1-101 Me 0 HHH Cl (= CHCO _Two Et) 1-102 Me 0 HHH Cl (= CHCO _Two Ph) 1-103 Me 0 HHH Cl (= C (Me) CO _Two Me) 1-104 Me 0 HHH Cl (= C (Me) CO _Two Et) 1-105 Me 0 HHH Cl (= C (Me) CO _Two Ph) 1-106 Me 0 HHH Cl (CO _Two (Me, Me) 1-107 Me 0 HHH Cl (CO _Two Me, Et) 1-108 Me 0 HHH Cl (CO _Two Me, Pr) 1-109 Me 0 HHH Cl (CO _Two Me, CH _Two CH = CH _Two ) 1-110 Me 0 HHH Cl (CO _Two Me, CH _Two OMe) 1-111 Me 0 HHH Cl (CO _Two Me, CH _Two OEt) 1-112 Me 0 HHH Cl (CO _Two Me, CH _Two SMe) 1-113 Me 0 HHH Cl (CO _Two Me, CH _Two CO _Two Me) 1-114 Me 0 HHH Cl (CO _Two Me, CH _Two CO _Two Et) 1-115 Me 0 HHH Cl (CO _Two Me, CH _Two CN) 1-116 Me 0 HHH Cl (CO _Two Me, CH _Two CF _Three ) 1-117 Me 0 HHH Cl (CO _Two Me, CH _Two OH) 1-118 Me 0 HHH Cl (CO _Two Me, CH _Two C≡CH) 1-119 Me 0 HHH Cl (CO _Two Me, COMe) 1-120 Me 0 HHH Cl (CO _Two Me, COEt) 1-121 Me 0 HHH Cl (CO _Two Me, CO _Two Me) 1-122 Me 0 HHH Cl (CO _Two Me, CO _Two Et) 1-123 Me 0 HHH Cl (CO _Two Me, COCO _Two Me) 1-124 Me 0 HHH Cl (CO _Two Me, SO _Two Me) 1-125 Me 0 HHH Cl (CO _Two Me, SO _Two NHMe) 1-126 Me 0 HHH Cl (CO _Two Me, SO _Two Ph) 1-127 Me 0 HHH Cl (CO _Two Et, Me) 1-128 Me 0 HHH Cl (CO _Two Et, Et) 1-129 Me 0 HHH Cl (CO _Two Et, Pr) 1-130 Me 0 HHH Cl (CO _Two Et, CH _Two CH = CH _Two ) 1-131 Me 0 HHH Cl (CO _Two Et, CH _Two OMe) 1-132 Me 0 HHH Cl (CO _Two Et, CH _Two OEt) 1-133 Me 0 HHH Cl (CO _Two Et, CH _Two SMe) 1-134 Me 0 HHH Cl (CO _Two Et, CH _Two CO _Two Me) 1-135 Me 0 HHH Cl (CO _Two Et, CH _Two CO _Two Et) 1-136 Me 0 HHH Cl (CO _Two Et, CH _Two CN) 1-137 Me 0 HHH Cl (CO _Two Et, CH _Two CF _Three ) 1-138 Me 0 HHH Cl (CO _Two Et, CH _Two OH) 1-139 Me 0 HHH Cl (CO _Two Et, CH _Two C≡CH) 1-140 Me 0 HHH Cl (CO _Two Et, CO _Two Et) 1-141 Me 0 HHH Cl (CO _Two Et, COCO _Two Me) 1-142 Me 0 HHH Cl (CO _Two Et, SO _Two Me) 1-143 Me 0 HHH Cl (CO _Two Et, SO _Two NHMe) 1-144 Me 0 HHH Cl (CO _Two Et, SO _Two Ph) 1-145 Me 2 HHH Cl (H, H) 1-146 Me 2 HHH Cl (H, COMe) 1-147 Me 2 HHH Cl (H, COEt) 1-148 Me 2 HHH Cl (H, COPr) 1-149 Me 2 HHH Cl (H, COiPr) 1-150 Me 2 HHH Cl (H, COBu) 1-151 Me 2 HHH Cl (H, COsBu) 1-152 Me 2 HHH Cl (H, COiBu) 1- 153 Me 2 HHH Cl (H, COtBu) 1-154 Me 2 HHH Cl (H, COC _Five H ₁₁ ) 1-155 Me 2 HHH Cl (H, COneoC _Five H ₁₁ ) 1-156 Me 2 HHH Cl (H, COC ₆ H ₁₃ ) 1-157 Me 2 HHH Cl (H, COC ₇ H ₁₅ ) 1-158 Me 2 HHH Cl (H, COC ₈ H ₁₇ ) 1-159 Me 2 HHH Cl (H, COC ₉ H ₁₉ ) 1-160 Me 2 HHH Cl (H, COcPr) 1-161 Me 2 HHH Cl (H, COcBu) 1-162 Me 2 HHH Cl (H, COcC _Five H ₉ ) 1-163 Me 2 HHH Cl (H, COcC ₆ H ₁₁ ) 1-164 Me 2 HHH Cl (H, COCH = CH _Two ) 1-165 Me 2 HHH Cl (H, COCH = CHPh) 1-166 Me 2 HHH Cl (H, COCH = CHMe) 1-167 Me 2 HHH Cl (H, COCH = CHCl) 1-168 Me 2 HHH Cl (H, COC≡CH) 1-169 Me 2 HHH Cl (H, COCH _Two CH = CH _Two ) 1-170 Me 2 HHH Cl (H, COCH _Two C≡CH) 1-171 Me 2 HHH Cl (H, COCH _Two F) 1-172 Me 2 HHH Cl (H, COCH _Two Cl) 1-173 Me 2 HHH Cl (H, COCH _Two Br) 1-174 Me 2 HHH Cl (H, COCH _Two OMe) 1-175 Me 2 HHH Cl (H, COCH _Two OEt) 1-176 Me 2 HHH Cl (H, COCH _Two OPh) 1-177 Me 2 HHH Cl (H, COCH _Two SMe) 1-178 Me 2 HHH Cl (H, COCH _Two SEt) 1-179 Me 2 HHH Cl (H, COCH _Two SPh) 1-180 Me 2 HHH Cl (H, COCH _Two CN) 1-181 Me 2 HHH Cl (H, CH _Two O (2-Pyr)) 1-182 Me 2 HHH Cl (H, CH _Two CO _Two Me) 1-183 Me 2 HHH Cl (H, CH _Two CO _Two Et) 1-184 Me 2 HHH Cl (H, COCH _Two CH _Two Cl) 1-185 Me 2 HHH Cl (H, COCH _Two CH _Two OMe) 1-186 Me 2 HHH Cl (H, COCH _Two CH _Two OEt) 1-187 Me 2 HHH Cl (H, COCH _Two CH _Two SMe) 1-188 Me 2 HHH Cl (H, COPh) 1-189 Me 2 HHH Cl (H, CO (4-Cl-Ph)) 1-190 Me 2 HHH Cl (H, CO (4-Me-Ph) )) 1-191 Me 2 HHH Cl (H, CO (2-Pyr)) 1-192 Me 2 HHH Cl (H, CO (3-Pyr)) 1-193 Me 2 HHH Cl (H, CO (4- Pyr)) 1-194 Me 2 HHH Cl (H, CO (2-Thi)) 1-195 Me 2 HHH Cl (H, CO (3-Thi)) 1-196 Me 2 HHH Cl (H, C (S ) Me) 1-197 Me 2 HHH Cl (H, C (S) Et) 1-198 Me 2 HHH Cl (H, C (S) Ph) 1-199 Me 2 HHH Cl (H, CO _Two Me) 1-200 Me 2 HHH Cl (H, CO _Two Et) 1-201 Me 2 HHH Cl (H, CO _Two Pr) 1-202 Me 2 HHH Cl (H, CO _Two iPr) 1-203 Me 2 HHH Cl (H, CO _Two Bu) 1-204 Me 2 HHH Cl (H, CO _Two iBu) 1-205 Me 2 HHH Cl (H, CO _Two tBu) 1-206 Me 2 HHH Cl (H, CO _Two CH _Two CH = CH _Two ) 1-207 Me 2 HHH Cl (H, CO _Two CH _Two CH _Two OMe) 1-208 Me 2 HHH Cl (H, CO _Two CH _Two CH _Two OEt) 1-209 Me 2 HHH Cl (H, CO _Two CH _Two CH _Two Cl) 1-210 Me 2 HHH Cl (H, CO _Two CH _Two CH _Two SMe) 1-211 Me 2 HHH Cl (H, CO _Two CH _Two CH _Two CN) 1-212 Me 2 HHH Cl (H, CO _Two CH _Two Cl) 1-213 Me 2 HHH Cl (H, CO _Two CHCl _Three ) 1-214 Me 2 HHH Cl (H, CO _Two CH _Two CCl _Three ) 1-215 Me 2 HHH Cl (H, CO _Two CH _Two CF _Three ) 1-216 Me 2 HHH Cl (H, CO _Two Ph) 1-217 Me 2 HHH Cl (H, COSMe) 1-218 Me 2 HHH Cl (H, COSEt) 1-219 Me 2 HHH Cl (H, COSPr) 1-220 Me 2 HHH Cl (H, CS _Two Me) 1-221 Me 2 HHH Cl (H, CS _Two Ph) 1-222 Me 2 HHH Cl (H, COCOMe) 1-223 Me 2 HHH Cl (H, COCOEt) 1-224 Me 2 HHH Cl (H, COCOPh) 1-225 Me 2 HHH Cl (H, COCO _Two Me) 1-226 Me 2 HHH Cl (H, COCO _Two Et) 1-227 Me 2 HHH Cl (H, COCO _Two Ph) 1-228 Me 2 HHH Cl (H, CONH _Two ) 1-229 Me 2 HHH Cl (H, CONHMe) 1-230 Me 2 HHH Cl (H, CONMe _Two ) 1-231 Me 2 HHH Cl (H, CONEt _Two ) 1-232 Me 2 HHH Cl (H, CONH (4-Cl-Ph)) 1-233 Me 2 HHH Cl (H, C (S) NHMe) 1-234 Me 2 HHH Cl (H, SO _Two NH _Two ) 1-235 Me 2 HHH Cl (H, SO _Two NHMe) 1-236 Me 2 HHH Cl (H, SO _Two NMe _Two ) 1-237 Me 2 HHH Cl (H, SO _Two Me) 1-238 Me 2 HHH Cl (H, SO _Two Et) 1-239 Me 2 HHH Cl (H, SO _Two Ph) 1-240 Me 2 HHH Cl (H, SO _Two (4-Me-Ph)) 1-241 Me 2 HHH Cl (= C (Me) NHMe) 1-242 Me 2 HHH Cl (= C (Me) NHEt) 1-243 Me 2 HHH Cl (= CHCO _Two Me) 1-244 Me 2 HHH Cl (= CHCO _Two Et) 1-245 Me 2 HHH Cl (= CHCO _Two Ph) 1-246 Me 2 HHH Cl (= C (Me) CO _Two Me) 1-247 Me 2 HHH Cl (= C (Me) CO _Two Et) 1-248 Me 2 HHH Cl (= C (Me) CO _Two Ph) 1-249 Me 2 HHH Cl (CO _Two Me, Me) 1-250 Me 2 HHH Cl (CO _Two Me, Et) 1-251 Me 2 HHH Cl (CO _Two Me, Pr) 1-252 Me 2 HHH Cl (CO _Two Me, CH _Two CH = CH _Two ) 1-253 Me 2 HHH Cl (CO _Two Me, CH _Two OMe) 1-254 Me 2 HHH Cl (CO _Two Me, CH _Two OEt) 1-255 Me 2 HHH Cl (CO _Two Me, CH _Two SMe) 1-256 Me 2 HHH Cl (CO _Two Me, CH _Two CO _Two Me) 1-257 Me 2 HHH Cl (CO _Two Me, CH _Two CO _Two Et) 1-258 Me 2 HHH Cl (CO _Two Me, CH _Two CN) 1-259 Me 2 HHH Cl (CO _Two Me, CH _Two CF _Three ) 1-260 Me 2 HHH Cl (CO _Two Me, CH _Two OH) 1-261 Me 2 HHH Cl (CO _Two Me, CH _Two C≡CH) 1-262 Me 2 HHH Cl (CO _Two Me, COMe) 1-263 Me 2 HHH Cl (CO _Two Me, COEt) 1-264 Me 2 HHH Cl (CO _Two Me, CO _Two Me) 1-265 Me 2 HHH Cl (CO _Two Me, CO _Two Et) 1-266 Me 2 HHH Cl (CO _Two Me, COCO _Two Me) 1-267 Me 2 HHH Cl (CO _Two Me, SO _Two Me) 1-268 Me 2 HHH Cl (CO _Two Me, SO _Two NHMe) 1-269 Me 2 HHH Cl (CO _Two Me, SO _Two Ph) 1-270 Me 2 HHH Cl (CO _Two Et, Me) 1-271 Me 2 HHH Cl (CO _Two Et, Et) 1-272 Me 2 HHH Cl (CO _Two Et, Pr) 1-273 Me 2 HHH Cl (CO _Two Et, CH _Two CH = CH _Two ) 1-274 Me 2 HHH Cl (CO _Two Et, CH _Two OMe) 1-275 Me 2 HHH Cl (CO _Two Et, CH _Two OEt) 1-276 Me 2 HHH Cl (CO _Two Et, CH _Two SMe) 1-277 Me 2 HHH Cl (CO _Two Et, CH _Two CO _Two Me) 1-278 Me 2 HHH Cl (CO _Two Et, CH _Two CO _Two Et) 1-279 Me 2 HHH Cl (CO _Two Et, CH _Two CN) 1-280 Me 2 HHH Cl (CO _Two Et, CH _Two CF _Three ) 1-281 Me 2 HHH Cl (CO _Two Et, CH _Two OH) 1-282 Me 2 HHH Cl (CO _Two Et, CH _Two C≡CH) 1-283 Me 2 HHH Cl (CO _Two Et, CO _Two Et) 1-284 Me 2 HHH Cl (CO _Two Et, COCO _Two Me) 1-285 Me 2 HHH Cl (CO _Two Et, SO _Two Me) 1-286 Me 2 HHH Cl (CO _Two Et, SO _Two NHMe) 1-287 Me 2 HHH Cl (CO _Two Et, SO _Two Ph) 1-288 Et 0 HHH Cl (H, H) 1-289 Et 1 HHH Cl (H, H) 1-290 Et 0 HHH Cl (H, COMe) 1-291 Et 0 HHH Cl (H, COEt) 1-292 Et 0 HHH Cl (H, COPr) 1-293 Et 0 HHH Cl (H, COiPr) 1-294 Et 0 HHH Cl (H, COBu) 1-295 Et 0 HHH Cl (H, COsBu) 1- 296 Et 0 HHH Cl (H, COiBu) 1-297 Et 0 HHH Cl (H, COtBu) 1-298 Et 0 HHH Cl (H, COC _Five H ₁₁ ) 1-299 Et 0 HHH Cl (H, COneoC _Five H ₁₁ ) 1-300 Et 0 HHH Cl (H, COC ₆ H ₁₃ ) 1-301 Et 0 HHH Cl (H, COC ₇ H ₁₅ ) 1-302 Et 0 HHH Cl (H, COC ₈ H ₁₇ ) 1-303 Et 0 HHH Cl (H, COC ₉ H ₁₉ ) 1-304 Et 0 HHH Cl (H, COcPr) 1-305 Et 0 HHH Cl (H, COcBu) 1-306 Et 0 HHH Cl (H, COcC _Five H ₉ ) 1-307 Et 0 HHH Cl (H, COcC ₆ H ₁₁ ) 1-308 Et 0 HHH Cl (H, COCH = CH _Two ) 1-309 Et 0 HHH Cl (H, COC (Me) = CH _Two ) 1-310 Et 0 HHH Cl (H, COCH = CHPh) 1-311 Et 0 HHH Cl (H, COCH = CHMe) 1-312 Et 0 HHH Cl (H, COCH = CHCl) 1-313 Et 0 HHH Cl (H, COC≡CH) 1-314 Et 0 HHH Cl (H, COCH _Two CH = CH _Two ) 1-315 Et 0 HHH Cl (H, COCH _Two C≡CH) 1-316 Et 0 HHH Cl (H, COCH _Two F) 1-317 Et 0 HHH Cl (H, COCH _Two Cl) 1-318 Et 0 HHH Cl (H, COCH _Two Br) 1-319 Et 0 HHH Cl (H, COCH _Two OMe) 1-320 Et 0 HHH Cl (H, COCH _Two OEt) 1-321 Et 0 HHH Cl (H, COCH _Two OPh) 1-322 Et 0 HHH Cl (H, COCH _Two SMe) 1-323 Et 0 HHH Cl (H, COCH _Two SEt) 1-324 Et 0 HHH Cl (H, COCH _Two SPh) 1-325 Et 0 HHH Cl (H, COCH _Two CN) 1-326 Et 0 HHH Cl (H, CH _Two O (2-Pyr)) 1-327 Et 0 HHH Cl (H, CH _Two CO _Two Me) 1-328 Et 0 HHH Cl (H, CH _Two CO _Two Et) 1-329 Et 0 HHH Cl (H, COCH _Two CH _Two Cl) 1-330 Et 0 HHH Cl (H, COCH _Two CH _Two OMe) 1-331 Et 0 HHH Cl (H, COCH _Two CH _Two OEt) 1-332 Et 0 HHH Cl (H, COCH _Two CH _Two SMe) 1-333 Et 0 HHH Cl (H, COPh) 1-334 Et 0 HHH Cl (H, CO (4-Cl-Ph)) 1-335 Et 0 HHH Cl (H, CO (4-Me-Ph )) 1-336 Et 0 HHH Cl (H, CO (2-Pyr)) 1-337 Et 0 HHH Cl (H, CO (3-Pyr)) 1-338 Et 0 HHH Cl (H, CO (4- Pyr)) 1-339 Et 0 HHH Cl (H, CO (2-Thi)) 1-340 Et 0 HHH Cl (H, CO (3-Thi)) 1-341 Et 0 HHH Cl (H, C (S ) Me) 1-342 Et 0 HHH Cl (H, C (S) Et) 1-343 Et 0 HHH Cl (H, C (S) Ph) 1-344 Et 0 HHH Cl (H, CO _Two Me) 1-345 Et 1 HHH Cl (H, CO _Two Me) 1-346 Et 0 HHH Cl (H, CO _Two Et) 1-347 Et 1 HHH Cl (H, CO _Two Et) 1-348 Et 0 HHH Cl (H, CO _Two Pr) 1-349 Et 0 HHH Cl (H, CO _Two iPr) 1-350 Et 0 HHH Cl (H, CO _Two Bu) 1-351 Et 0 HHH Cl (H, CO _Two iBu) 1-352 Et 0 HHH Cl (H, CO _Two tBu) 1-353 Et 0 HHH Cl (H, CO _Two CH _Two CH = CH _Two ) 1-354 Et 0 HHH Cl (H, CO _Two CH _Two CH _Two OMe) 1-355 Et 0 HHH Cl (H, CO _Two CH _Two CH _Two OEt) 1-356 Et 0 HHH Cl (H, CO _Two CH _Two CH _Two Cl) 1-357 Et 0 HHH Cl (H, CO _Two CH _Two CH _Two SMe) 1-358 Et 0 HHH Cl (H, CO _Two CH _Two CH _Two CN) 1-359 Et 0 HHH Cl (H, CO _Two CH _Two Cl) 1-360 Et 0 HHH Cl (H, CO _Two CHClCH _Three ) 1-361 Et 0 HHH Cl (H, CO _Two CH _Two CCl _Three ) 1-362 Et 0 HHH Cl (H, CO _Two CH _Two CF _Three ) 1-363 Et 0 HHH Cl (H, CO _Two Ph) 1-364 Et 0 HHH Cl (H, COSMe) 1-365 Et 0 HHH Cl (H, COSEt) 1-366 Et 0 HHH Cl (H, COSPr) 1-367 Et 0 HHH Cl (H, CS _Two Me) 1-368 Et 0 HHH Cl (H, CS _Two Ph) 1-369 Et 0 HHH Cl (H, COCOMe) 1-370 Et 0 HHH Cl (H, COCOEt) 1-371 Et 0 HHH Cl (H, COCOPh) 1-372 Et 0 HHH Cl (H, COCO _Two Me) 1-373 Et 0 HHH Cl (H, COCO _Two Et) 1-374 Et 0 HHH Cl (H, COCO _Two Ph) 1-375 Et 0 HHH Cl (H, CONH _Two ) 1-376 Et 0 HHH Cl (H, CONHMe) 1-377 Et 0 HHH Cl (H, CONMe _Two ) 1-378 Et 0 HHH Cl (H, CONEt _Two ) 1-379 Et 0 HHH Cl (H, CONH (4-Cl-Ph)) 1-380 Et 0 HHH Cl (H, SO _Two NH _Two ) 1-381 Et 0 HHH Cl (H, SO _Two NHMe) 1-382 Et 0 HHH Cl (H, SO _Two NMe _Two ) 1-383 Et 0 HHH Cl (H, SO _Two NHCH _Two CH = CH _Two ) 1-384 Et 0 HHH Cl (H, SO _Two Me) 1-385 Et 0 HHH Cl (H, SO _Two Et) 1-386 Et 0 HHH Cl (H, SO _Two Ph) 1-387 Et 0 HHH Cl (H, SO _Two (4-Me-Ph)) 1-388 Et 0 HHH Cl (= C (Me) NHMe) 1-389 Et 0 HHH Cl (= CHCO _Two Me) 1-390 Et 0 HHH Cl (= CHCO _Two Et) 1-391 Et 0 HHH Cl (= CHCO _Two Ph) 1-392 Et 0 HHH Cl (= C (Me) CO _Two Me) 1-393 Et 0 HHH Cl (= C (Me) CO _Two Et) 1-394 Et 0 HHH Cl (= C (Me) CO _Two Ph) 1-395 Et 0 HHH Cl (CO _Two Me, Me) 1-396 Et 0 HHH Cl (CO _Two Me, Et) 1-397 Et 0 HHH Cl (CO _Two Me, Pr) 1-398 Et 0 HHH Cl (CO _Two Me, CH _Two CH = CH _Two ) 1-399 Et 0 HHH Cl (CO _Two Me, CH _Two OMe) 1-400 Et 0 HHH Cl (CO _Two Me, CH _Two OEt) 1-401 Et 0 HHH Cl (CO _Two Me, CH _Two SMe) 1-402 Et 0 HHH Cl (CO _Two Me, CH _Two CO _Two Me) 1-403 Et 0 HHH Cl (CO _Two Me, CH _Two CO _Two Et) 1-404 Et 0 HHH Cl (CO _Two Me, CH _Two CN) 1-405 Et 0 HHH Cl (CO _Two Me, CH _Two CF _Three ) 1-406 Et 0 HHH Cl (CO _Two Me, CH _Two OH) 1-407 Et 0 HHH Cl (CO _Two Me, CH _Two C≡CH) 1-408 Et 0 HHH Cl (CO _Two Me, COMe) 1-409 Et 0 HHH Cl (CO _Two Me, COEt) 1-410 Et 0 HHH Cl (CO _Two Me, CO _Two Me) 1-411 Et 0 HHH Cl (CO _Two Me, CO _Two Et) 1-412 Et 0 HHH Cl (CO _Two Me, COCO _Two Me) 1-413 Et 0 HHH Cl (CO _Two Me, SO _Two Me) 1-414 Et 0 HHH Cl (CO _Two Me, SO _Two NHMe) 1-415 Et 0 HHH Cl (CO _Two Me, SO _Two Ph) 1-416 Et 0 HHH Cl (CO _Two Et, Me) 1-417 Et 0 HHH Cl (CO _Two Et, Et) 1-418 Et 0 HHH Cl (CO _Two Et, Pr) 1-419 Et 0 HHH Cl (CO _Two Et, CH _Two CH = CH _Two ) 1-420 Et 0 HHH Cl (CO _Two Et, CH _Two OMe) 1-421 Et 0 HHH Cl (CO _Two Et, CH _Two OEt) 1-422 Et 0 HHH Cl (CO _Two Et, CH _Two SMe) 1-423 Et 0 HHH Cl (CO _Two Et, CH _Two CO _Two Me) 1-424 Et 0 HHH Cl (CO _Two Et, CH _Two CO _Two Et) 1-425 Et 0 HHH Cl (CO _Two Et, CH _Two CN) 1-426 Et 0 HHH Cl (CO _Two Et, CH _Two CF _Three ) 1-427 Et 0 HHH Cl (CO _Two Et, CH _Two OH) 1-428 Et 0 HHH Cl (CO _Two Et, CH _Two C≡CH) 1-429 Et 0 HHH Cl (CO _Two Et, COMe) 1-430 Et 0 HHH Cl (CO _Two Et, COEt) 1-431 Et 0 HHH Cl (CO _Two Et, CO _Two Et) 1-432 Et 0 HHH Cl (CO _Two Et, COCO _Two Me) 1-433 Et 0 HHH Cl (CO _Two Et, SO _Two Me) 1-434 Et 0 HHH Cl (CO _Two Et, SO _Two NHMe) 1-435 Et 0 HHH Cl (CO _Two Et, SO _Two Ph) 1-436 Et 0 HHH Cl (CO _Two Et, SO _Two (4-Me-Ph)) 1-437 Et 2 HHH Cl (H, H) 1-438 Et 2 HHH Cl (H, COMe) 1-439 Et 2 HHH Cl (H, COEt) 1-440 Et 2 HHH Cl (H, COPr) 1-441 Et 2 HHH Cl (H, COiPr) 1-442 Et 2 HHH Cl (H, COBu) 1-443 Et 2 HHH Cl (H, COsBu) 1-444 Et 2 HHH Cl ( (H, COiBu) 1-445 Et 2 HHH Cl (H, COtBu) 1-446 Et 2 HHH Cl (H, COC _Five H ₁₁ ) 1-447 Et 2 HHH Cl (H, COneoC _Five H ₁₁ ) 1-448 Et 2 HHH Cl (H, COC ₆ H ₁₃ ) 1-449 Et 2 HHH Cl (H, COC ₇ H ₁₅ ) 1-450 Et 2 HHH Cl (H, COC ₈ H ₁₇ ) 1-451 Et 2 HHH Cl (H, COC ₉ H ₁₉ ) 1-452 Et 2 HHH Cl (H, COcPr) 1-453 Et 2 HHH Cl (H, COcBu) 1-454 Et 2 HHH Cl (H, COcC _Five H ₉ ) 1-455 Et 2 HHH Cl (H, COcC ₆ H ₁₁ ) 1-456 Et 2 HHH Cl (H, COCH = CH _Two ) 1-457 Et 2 HHH Cl (H, COCH = CHPh) 1-458 Et 2 HHH Cl (H, COCH = CHMe) 1-459 Et 2 HHH Cl (H, COCH = CHCl) 1-460 Et 2 HHH Cl (H, COC≡CH) 1-461 Et 2 HHH Cl (H, COCH _Two CH = CH _Two ) 1-462 Et 2 HHH Cl (H, COCH _Two C≡CH) 1-463 Et 2 HHH Cl (H, COCH _Two F) 1-464 Et 2 HHH Cl (H, COCH _Two Cl) 1-465 Et 2 HHH Cl (H, COCH _Two Br) 1-466 Et 2 HHH Cl (H, COCH _Two OMe) 1-467 Et 2 HHH Cl (H, COCH _Two OEt) 1-468 Et 2 HHH Cl (H, COCH _Two OPh) 1-469 Et 2 HHH Cl (H, COCH _Two SMe) 1-470 Et 2 HHH Cl (H, COCH _Two SEt) 1-471 Et 2 HHH Cl (H, COCH _Two SPh) 1-472 Et 2 HHH Cl (H, COCH _Two CN) 1-473 Et 2 HHH Cl (H, CH _Two O (2-Pyr)) 1-474 Et 2 HHH Cl (H, CH _Two CO _Two Me) 1-475 Et 2 HHH Cl (H, CH _Two CO _Two Et) 1-476 Et 2 HHH Cl (H, COCH _Two CH _Two Cl) 1-477 Et 2 HHH Cl (H, COCH _Two CH _Two OMe) 1-478 Et 2 HHH Cl (H, COCH _Two CH _Two OEt) 1-479 Et 2 HHH Cl (H, COCH _Two CH _Two SMe) 1-480 Et 2 HHH Cl (H, COPh) 1-481 Et 2 HHH Cl (H, CO (4-Cl-Ph)) 1-482 Et 2 HHH Cl (H, CO (4-Me-Ph )) 1-483 Et 2 HHH Cl (H, CO (2-Pyr)) 1-484 Et 2 HHH Cl (H, CO (3-Pyr)) 1-485 Et 2 HHH Cl (H, CO (4- Pyr)) 1-486 Et 2 HHH Cl (H, CO (2-Thi)) 1-487 Et 2 HHH Cl (H, CO (3-Thi)) 1-488 Et 2 HHH Cl (H, C (S ) Me) 1-489 Et 2 HHH Cl (H, C (S) Et) 1-490 Et 2 HHH Cl (H, C (S) Ph) 1-491 Et 2 HHH Cl (H, CO _Two Me) 1-492 Et 2 HHH Cl (H, CO _Two Et) 1-493 Et 2 HHH Cl (H, CO _Two Pr) 1-494 Et 2 HHH Cl (H, CO _Two iPr) 1-495 Et 2 HHH Cl (H, CO _Two Bu) 1-496 Et 2 HHH Cl (H, CO _Two iBu) 1-497 Et 2 HHH Cl (H, CO _Two tBu) 1-498 Et 2 HHH Cl (H, CO _Two CH _Two CH = CH _Two ) 1-499 Et 2 HHH Cl (H, CO _Two CH _Two CH _Two OMe) 1-500 Et 2 HHH Cl (H, CO _Two CH _Two CH _Two OEt) 1-501 Et 2 HHH Cl (H, CO _Two CH _Two CH _Two Cl) 1-502 Et 2 HHH Cl (H, CO _Two CH _Two CH _Two SMe) 1-503 Et 2 HHH Cl (H, CO _Two CH _Two CH _Two CN) 1-504 Et 2 HHH Cl (H, CO _Two CH _Two Cl) 1-505 Et 2 HHH Cl (H, CO _Two CHCl _Three ) 1-506 Et 2 HHH Cl (H, CO _Two CH _Two CCl _Three ) 1-507 Et 2 HHH Cl (H, CO _Two CH _Two CF _Three ) 1-508 Et 2 HHH Cl (H, CO _Two Ph) 1-509 Et 2 HHH Cl (H, COSMe) 1-510 Et 2 HHH Cl (H, COSEt) 1-511 Et 2 HHH Cl (H, COSPr) 1-512 Et 2 HHH Cl (H, C ( S) SMe) 1-513 Et 2 HHH Cl (H, C (S) SPh) 1-514 Et 2 HHH Cl (H, COCOMe) 1-515 Et 2 HHH Cl (H, COCOEt) 1-516 Et 2 HHH Cl (H, COCOPh) 1-517 Et 2 HHH Cl (H, COCOPh) _Two Me) 1-518 Et 2 HHH Cl (H, COCO _Two Et) 1-519 Et 2 HHH Cl (H, COCO _Two Ph) 1-520 Et 2 HHH Cl (H, CONH _Two ) 1-521 Et 2 HHH Cl (H, CONHMe) 1-522 Et 2 HHH Cl (H, CONMe _Two ) 1-523 Et 2 HHH Cl (H, CONEt _Two ) 1-524 Et 2 HHH Cl (H, SO _Two NH _Two ) 1-525 Et 2 HHH Cl (H, SO _Two NHMe) 1-526 Et 2 HHH Cl (H, SO _Two NMe _Two ) 1-527 Et 2 HHH Cl (H, SO _Two Me) 1-528 Et 2 HHH Cl (H, SO _Two Et) 1-529 Et 2 HHH Cl (H, SO _Two Ph) 1-530 Et 2 HHH Cl (H, SO _Two (4-Me-Ph)) 1-531 Et 2 HHH Cl (= C (Me) NHMe) 1-532 Et 2 HHH Cl (= CHCO _Two Me) 1-533 Et 2 HHH Cl (= CHCO _Two Et) 1-534 Et 2 HHH Cl (= CHCO _Two Ph) 1-535 Et 2 HHH Cl (= C (Me) CO _Two Me) 1-536 Et 2 HHH Cl (= C (Me) CO _Two Et) 1-537 Et 2 HHH Cl (= C (Me) CO _Two Ph) 1-538 Et 2 HHH Cl (CO _Two Me, Me) 1-539 Et 2 HHH Cl (CO _Two Me, Et) 1-540 Et 2 HHH Cl (CO _Two Me, Pr) 1-541 Et 2 HHH Cl (CO _Two Me, CH _Two CH = CH _Two ) 1-542 Et 2 HHH Cl (CO _Two Me, CH _Two OMe) 1-543 Et 2 HHH Cl (CO _Two Me, CH _Two OEt) 1-544 Et 2 HHH Cl (CO _Two Me, CH _Two SMe) 1-545 Et 2 HHH Cl (CO _Two Me, CH _Two CO _Two Me) 1-546 Et 2 HHH Cl (CO _Two Me, CH _Two CO _Two Et) 1-547 Et 2 HHH Cl (CO _Two Me, CH _Two CN) 1-548 Et 2 HHH Cl (CO _Two Me, CH _Two CF _Three ) 1-549 Et 2 HHH Cl (CO _Two Me, CH _Two OH) 1-550 Et 2 HHH Cl (CO _Two Me, CH _Two C≡CH) 1-551 Et 2 HHH Cl (CO _Two Me, COMe) 1-552 Et 2 HHH Cl (CO _Two Me, COEt) 1-553 Et 2 HHH Cl (CO _Two Me, CO _Two Me) 1-554 Et 2 HHH Cl (CO _Two Me, CO _Two Et) 1-555 Et 2 HHH Cl (CO _Two Me, COCO _Two Me) 1-556 Et 2 HHH Cl (CO _Two Me, SO _Two Me) 1-557 Et 2 HHH Cl (CO _Two Me, SO _Two NHMe) 1-558 Et 2 HHH Cl (CO _Two Me, SO _Two Ph) 1-559 Et 2 HHH Cl (CO _Two Et, Me) 1-560 Et 2 HHH Cl (CO _Two Et, Et) 1-561 Et 2 HHH Cl (CO _Two Et, Pr) 1-562 Et 2 HHH Cl (CO _Two Et, CH _Two CH = CH _Two ) 1-563 Et 2 HHH Cl (CO _Two Et, CH _Two OMe) 1-564 Et 2 HHH Cl (CO _Two Et, CH _Two OEt) 1-565 Et 2 HHH Cl (CO _Two Et, CH _Two SMe) 1-566 Et 2 HHH Cl (CO _Two Et, CH _Two CO _Two Me) 1-567 Et 2 HHH Cl (CO _Two Et, CH _Two CO _Two Et) 1-568 Et 2 HHH Cl (CO _Two Et, CH _Two CN) 1-569 Et 2 HHH Cl (CO _Two Et, CH _Two CF _Three ) 1-570 Et 2 HHH Cl (CO _Two Et, CH _Two OH) 1-571 Et 2 HHH Cl (CO _Two Et, CH _Two C≡CH) 1-572 Et 2 HHH Cl (CO _Two Et, COMe) 1-573 Et 2 HHH Cl (CO _Two Et, COEt) 1-574 Et 2 HHH Cl (CO _Two Et, CO _Two Et) 1-575 Et 2 HHH Cl (CO _Two Et, COCO _Two Me) 1-576 Et 2 HHH Cl (CO _Two Et, SO _Two Me) 1-577 Et 2 HHH Cl (CO _Two Et, SO _Two NHMe) 1-578 Et 2 HHH Cl (CO _Two Et, SO _Two Ph) 1-579 CF _Three 0 HHH Cl (H, H) 1-580 CF _Three 0 HHH Cl (H, COMe) 1-581 CF _Three 0 HHH Cl (H, COEt) 1-582 CF _Three 0 HHH Cl (H, CO _Two Me) 1-583 CF _Three 0 HHH Cl (H, CO _Two Et) 1-584 CH _Two CF _Three 0 HHH Cl (H, H) 1-585 CH _Two CF _Three 0 HHH Cl (H, COMe) 1-586 CH _Two CF _Three 0 HHH Cl (H, COEt) 1-587 CH _Two CF _Three 0 HHH Cl (H, CO _Two Me) 1-588 CH _Two CF _Three 0 HHH Cl (H, CO _Two Et) 1-589 CF _Two CF _Three 0 HHH Cl (H, H) 1-590 CF _Two CF _Three 0 HHH Cl (H, COMe) 1-591 CF _Two CF _Three 0 HHH Cl (H, COEt) 1-592 CF _Two CF _Three 0 HHH Cl (H, CO _Two Me) 1-593 CF _Two CF _Three 0 HHH Cl (H, CO _Two Et) 1-594 Pr 0 HHH Cl (H, H) 1-595 Pr 0 HHH Cl (H, COMe) 1-596 Pr 0 HHH Cl (H, COEt) 1-597 Pr 0 HHH Cl (H, CO _Two Me) 1-598 Pr 0 HHH Cl (H, CO _Two Et) 1-599 iPr 0 HHH Cl (H, H) 1-600 iPr 0 HHH Cl (H, COMe) 1-601 iPr 0 HHH Cl (H, COEt) 1-602 iPr 0 HHH Cl (H, CO _Two Me) 1-603 iPr 0 HHH Cl (H, CO _Two Et) 1-604 Bu 0 HHH Cl (H, H) 1-605 Bu 0 HHH Cl (H, COMe) 1-606 Bu 0 HHH Cl (H, COEt) 1-607 Bu 0 HHH Cl (H, CO _Two Me) 1-608 Bu 0 HHH Cl (H, CO _Two Et) 1-609 tBu 0 HHH Cl (H, H) 1-610 tBu 0 HHH Cl (H, COMe) 1-611 tBu 0 HHH Cl (H, COEt) 1-612 tBu 0 HHH Cl (H, CO _Two Me) 1-613 tBu 0 HHH Cl (H, CO _Two Et) 1-614 Me 0 HH 4-Cl Cl (H, H) 1-615 Me 0 HH 4-Cl Cl (H, COMe) 1-616 Me 0 HH 4-Cl Cl (H, COEt) 1-617 Me 0 HH 4-Cl Cl (H, CO _Two Me) 1-618 Me 0 HH 4-Cl Cl (H, CO _Two Et) 1-619 Et 0 HH 4-Cl Cl (H, H) 1-620 Et 0 HH 4-Cl Cl (H, COMe) 1-621 Et 0 HH 4-Cl Cl (H, COEt) 1-622 Et 0 HH 4-Cl Cl (H, CO _Two Me) 1-623 Et 0 HH 4-Cl Cl (H, CO _Two Et) 1-624 Me 0 HH 4-Br Cl (H, H) 1-625 Me 0 HH 4-Br Cl (H, COMe) 1-626 Me 0 HH 4-Br Cl (H, COEt) 1-627 Me 0 HH 4-Br Cl (H, CO _Two Me) 1-628 Me 0 HH 4-Br Cl (H, CO _Two Et) 1-629 Et 0 HH 4-Br Cl (H, H) 1-630 Et 0 HH 4-Br Cl (H, COMe) 1-631 Et 0 HH 4-Br Cl (H, COEt) 1-632 Et 0 HH 4-Br Cl (H, CO _Two Me) 1-633 Et 0 HH 4-Br Cl (H, CO _Two Et) 1-634 Me 0 HH 4-CN Cl (H, H) 1-635 Me 0 HH 4-CN Cl (H, CO _Two Me) 1-636 Me 0 HH 4-CN Cl (H, CO _Two Et) 1-637 Et 0 HH 4-CN Cl (H, H) 1-638 Et 0 HH 4-CN Cl (H, CO _Two Me) 1-639 Et 0 HH 4-CN Cl (H, CO _Two Et) 1-640 Me 0 HH 4-CF _Three Cl (H, H) 1-641 Me 0 HH 4-CF _Three Cl (H, CO _Two Me) 1-642 Me 0 HH 4-CF _Three Cl (H, CO _Two Et) 1-643 Et 0 HH 4-CF _Three Cl (H, H) 1-644 Et 0 HH 4-CF _Three Cl (H, CO _Two Me) 1-645 Et 0 HH 4-CF _Three Cl (H, CO _Two Et) 1-646 Et 0 HH 4-I Cl (H, H) 1-647 Et 0 HH 4-I Cl (H, CO _Two Me) 1-648 Et 0 HH 4-I Cl (H, CO _Two Et) 1-649 Et 0 HH 4-MeO Cl (H, H) 1-650 Et 0 HH 4-MeO Cl (H, CO _Two Me) 1-651 Et 0 HH 4-MeO Cl (H, CO _Two Et) 1-652 CH _Two CH = CH _Two 0 HHH Cl (H, H) 1-653 CH _Two CH = CH _Two 0 HHH Cl (H, CO _Two Me) 1-654 CH _Two CH = CH _Two 0 HHH Cl (H, CO _Two Et) 1-655 Me 0 HHH Cl (H, CONHEt) 1-656 Me 0 HHH Cl (H, CONHPr) 1-657 Me 0 HHH Cl (H, CONHiPr) 1-658 Me 0 HHH Cl (H, CONHBu) 1-659 Me 0 HHH Cl (H, CONHisBu) 1-660 Me 0 HHH Cl (H, CONHsBu) 1-661 Me 0 HHH Cl (H, CONHtBu) 1-662 Et 0 HHH Cl (H, CONHEt) 1- 663 Et 0 HHH Cl (H, CONHPr) 1-664 Et 0 HHH Cl (H, CONHiPr) 1-665 Et 0 HHH Cl (H, CONHBu) 1-666 Et 0 HHH Cl (H, CONHiBu) 1-667 Et 0 HHH Cl (H, CONHsBu) 1-668 Et 0 HHH Cl (H, CONHtBu) 1-669 Me 2 HHH Cl (H, CONHEt) 1-670 Me 2 HHH Cl (H, CONHPr) 1-671 Me 2 HHH Cl (H, CONHiPr) 1-672 Me 2 HHH Cl (H, CONHBu) 1-673 Me 2 HHH Cl (H, CONHiBu) 1-674 Me 2 HHH Cl (H, CONHsBu) 1-675 Me 2 HHH Cl ( (H, CONHtBu) 1-676 Et 2 HHH Cl (H, CONHEt) 1-677 Et 2 HHH Cl (H, CONHPr) 1-678 Et 2 HHH Cl (H, CONHiPr) 1-679 Et 2 HHH Cl (H, CONHBu) 1-680 Et 2 HHH Cl (H, CONHiBu) 1-681 Et 2 HHH Cl (H, CONHsBu) 1-682 Et 2 HHH Cl (H, CONHtBu) 1-1001 Me 0 HHH Br (H, H) 1-1002 Me 0 HHH Br (H, COMe) 1-1003 Me 0 HHH Br (H, COEt) 1-1004 Me 0 HHH Br (H, COPr) 1-1005 Me 0 HHH Br (H, COiPr) 1- 1006 Me 0 HHH Br (H, COBu) 1- 1007 Me 0 HHH Br (H, COsBu) 1-1008 Me 0 HHH Br (H, COiBu) 1-1009 Me 0 HHH Br (H, COtBu) 1-1010 Me 0 HHH Br (H, COcPr) 1-1011 Me 0 HHH Br (H, COCH = CH _Two ) 1-1012 Me 0 HHH Br (H, COCH = CHMe) 1-1013 Me 0 HHH Br (H, COCH = CHCl) 1-1014 Me 0 HHH Br (H, COC≡CH) 1-1015 Me 0 HHH Br (H, COC≡CMe) 1-1016 Me 0 HHH Br (H, COCH _Two CH = CH _Two ) 1-1017 Me 0 HHH Br (H, COCH _Two C≡CH) 1-1018 Me 0 HHH Br (H, COCH _Two F) 1-1019 Me 0 HHH Br (H, COCH _Two Cl) 1-1020 Me 0 HHH Br (H, COCH _Two Br) 1-1021 Me 0 HHH Br (H, COCH _Two OMe) 1-1022 Me 0 HHH Br (H, COCH _Two OEt) 1-1025 Me 0 HHH Br (H, COCH _Two CN) 1-1026 Me 0 HHH Br (H, CH _Two CO _Two Me) 1-1027 Me 0 HHH Br (H, CH _Two CO _Two Et) 1-1028 Me 0 HHH Br (H, COCH _Two CH _Two Cl) 1-1029 Me 0 HHH Br (H, COCH _Two CH _Two OMe) 1-1030 Me 0 HHH Br (H, COCH _Two CH _Two OEt) 1-1031 Me 0 HHH Br (H, CO _Two Me) 1-1032 Me 1 HHH Br (H, CO _Two Me) 1-1033 Me 0 HHH Br (H, CO _Two Et) 1-1034 Me 1 HHH Br (H, CO _Two Et) 1-1035 Me 0 HHH Br (H, CO _Two Pr) 1-1036 Me 0 HHH Br (H, CO _Two iPr) 1-1037 Me 0 HHH Br (H, CO _Two Bu) 1-1038 Me 0 HHH Br (H, CO _Two iBu) 1-1039 Me 0 HHH Br (H, CO _Two tBu) 1-1040 Me 0 HHH Br (H, CO _Two CH _Two CH = CH _Two ) 1-1041 Me 0 HHH Br (H, CO _Two CH _Two CH _Two OMe) 1-1042 Me 0 HHH Br (H, CO _Two CH _Two CH _Two OEt) 1-1043 Me 0 HHH Br (H, CO _Two CH _Two CH _Two Cl) 1-1044 Me 0 HHH Br (H, CO _Two CH _Two CH _Two CN) 1-1045 Me 0 HHH Br (H, CO _Two CH _Two Cl) 1-1046 Me 0 HHH Br (H, CO _Two CHClMe) 1-1047 Me 0 HHH Br (H, CO _Two CH _Two CCl _Three ) 1-1048 Me 0 HHH Br (H, CO _Two CH _Two CF _Three ) 1-1049 Me 0 HHH Br (H, COCOMe) 1-1050 Me 0 HHH Br (H, COCOEt) 1-1051 Me 0 HHH Br (H, COCOe) _Two Me) 1-1052 Me 0 HHH Br (H, COCO _Two Et) 1-1053 Me 0 HHH Br (CO _Two (Me, Me) 1-1054 Me 0 HHH Br (CO _Two Me, Et) 1-1055 Me 0 HHH Br (CO _Two Me, Pr) 1-1056 Me 0 HHH Br (CO _Two Me, CH _Two CH = CH _Two ) 1-1057 Me 0 HHH Br (CO _Two Me, CH _Two OMe) 1-1058 Me 0 HHH Br (CO _Two Me, CH _Two OEt) 1-1059 Me 0 HHH Br (CO _Two Me, CH _Two CO _Two Me) 1-1060 Me 0 HHH Br (CO _Two Me, CH _Two CO _Two Et) 1-1061 Me 0 HHH Br (CO _Two Me, CH _Two CN) 1-1062 Me 0 HHH Br (CO _Two Me, CH _Two CF _Three ) 1-1063 Me 0 HHH Br (CO _Two Me, CH _Two C≡CH) 1-1064 Me 0 HHH Br (CO _Two Me, COMe) 1-1065 Me 0 HHH Br (CO _Two Me, COEt) 1-1066 Me 0 HHH Br (CO _Two Me, CO _Two Me) 1-1067 Me 0 HHH Br (CO _Two Me, CO _Two Et) 1-1068 Me 0 HHH Br (CO _Two Me, COCO _Two Me) 1-1069 Me 0 HHH Br (CO _Two Et, Me) 1-1070 Me 0 HHH Br (CO _Two Et, Et) 1-1071 Me 0 HHH Br (CO _Two Et, Pr) 1-1072 Me 0 HHH Br (CO _Two Et, CH _Two CH = CH _Two ) 1-1073 Me 0 HHH Br (CO _Two Et, CH _Two OMe) 1-1074 Me 0 HHH Br (CO _Two Et, CH _Two OEt) 1-1075 Me 0 HHH Br (CO _Two Et, CH _Two CO _Two Me) 1-1076 Me 0 HHH Br (CO _Two Et, CH _Two CO _Two Et) 1-1077 Me 0 HHH Br (CO _Two Et, CH _Two CN) 1-1078 Me 0 HHH Br (CO _Two Et, CH _Two CF _Three ) 1-1079 Me 0 HHH Br (CO _Two Et, CH _Two C≡CH) 1-1080 Me 0 HHH Br (CO _Two Et, CO _Two Et) 1-1081 Me 0 HHH Br (CO _Two Et, COCO _Two Me) 1-1082 Me 2 HHH Br (H, H) 1-1083 Me 2 HHH Br (H, COMe) 1-1084 Me 2 HHH Br (H, COEt) 1-1085 Me 2 HHH Br (H, COPr) 1-1086 Me 2 HHH Br (H, COiBu) 1-1087 Me 2 HHH Br (H, COBu) 1-1088 Me 2 HHH Br (H, COiBu) 1090 Me 2 HHH Br (H, COtBu) 1-1091 Me 2 HHH Br (H, COcPr) 1-1092 Me 2 HHH Br (H, COCH = CH _Two ) 1-1093 Me 2 HHH Br (H, COCH = CHMe) 1-1094 Me 2 HHH Br (H, COCH = CHCl) 1-1095 Me 2 HHH Br (H, COC≡CH) 1-1096 Me 2 HHH Br (H, COCH _Two CH = CH _Two ) 1-1097 Me 2 HHH Br (H, COCH _Two C≡CH) 1-1098 Me 2 HHH Br (H, COCH _Two F) 1-1099 Me 2 HHH Br (H, COCH _Two Cl) 1-1100 Me 2 HHH Br (H, COCH _Two Br) 1-1101 Me 2 HHH Br (H, COCH _Two OMe) 1-1102 Me 2 HHH Br (H, COCH _Two OEt) 1-1103 Me 2 HHH Br (H, COCH _Two CN) 1-1104 Me 2 HHH Br (H, CH _Two CO _Two Me) 1-1105 Me 2 HHH Br (H, CH _Two CO _Two Et) 1-1106 Me 2 HHH Br (H, COCH _Two CH _Two Cl) 1-1107 Me 2 HHH Br (H, COCH _Two CH _Two OMe) 1-1108 Me 2 HHH Br (H, COCH _Two CH _Two OEt) 1-1109 Me 2 HHH Br (H, CO _Two Me) 1-1110 Me 2 HHH Br (H, CO _Two Et) 1-1111 Me 2 HHH Br (H, CO _Two Pr) 1-1112 Me 2 HHH Br (H, CO _Two iPr) 1-1113 Me 2 HHH Br (H, CO _Two Bu) 1-1114 Me 2 HHH Br (H, CO _Two iBu) 1-1115 Me 2 HHH Br (H, CO _Two tBu) 1-1116 Me 2 HHH Br (H, CO _Two CH _Two CH = CH _Two ) 1-1117 Me 2 HHH Br (H, CO _Two CH _Two CH _Two OMe) 1-1118 Me 2 HHH Br (H, CO _Two CH _Two CH _Two OEt) 1-1119 Me 2 HHH Br (H, CO _Two CH _Two CH _Two Cl) 1-1120 Me 2 HHH Br (H, CO _Two CH _Two CH _Two CN) 1-1121 Me 2 HHH Br (H, CO _Two CH _Two Cl) 1-1122 Me 2 HHH Br (H, CO _Two CHCl _Three ) 1-1123 Me 2 HHH Br (H, CO _Two CH _Two CCl _Three ) 1-1124 Me 2 HHH Br (H, CO _Two CH _Two CF _Three ) 1-1125 Me 2 HHH Br (H, COCOe) 1-1126 Me 2 HHH Br (H, COCOEt) 1-1127 Me 2 HHH Br (H, COCOe) _Two Me) 1-1128 Me 2 HHH Br (H, COCO _Two Et) 1-1129 Me 2 HHH Br (CO _Two (Me, Me) 1-1130 Me 2 HHH Br (CO _Two Me, Et) 1-1131 Me 2 HHH Br (CO _Two Me, Pr) 1-1132 Me 2 HHH Br (CO _Two Me, CH _Two CH = CH _Two ) 1-1133 Me 2 HHH Br (CO _Two Me, CH _Two OMe) 1-1134 Me 2 HHH Br (CO _Two Me, CH _Two OEt) 1-1135 Me 2 HHH Br (CO _Two Me, CH _Two CO _Two Me) 1-1136 Me 2 HHH Br (CO _Two Me, CH _Two CO _Two Et) 1-1137 Me 2 HHH Br (CO _Two Me, CH _Two CN) 1-1138 Me 2 HHH Br (CO _Two Me, CH _Two CF _Three ) 1-1139 Me 2 HHH Br (CO _Two Me, CH _Two C≡CH) 1-1140 Me 2 HHH Br (CO _Two Me, COMe) 1-1141 Me 2 HHH Br (CO _Two Me, COEt) 1-1142 Me 2 HHH Br (CO _Two Me, CO _Two Me) 1-1143 Me 2 HHH Br (CO _Two Me, CO _Two Et) 1-1144 Me 2 HHH Br (CO _Two Me, COCO _Two Me) 1-1145 Me 2 HHH Br (CO _Two Et, Me) 1-1146 Me 2 HHH Br (CO _Two Et, Et) 1-1147 Me 2 HHH Br (CO _Two Et, Pr) 1-1148 Me 2 HHH Br (CO _Two Et, CH _Two CH = CH _Two ) 1-1149 Me 2 HHH Br (CO _Two Et, CH _Two OMe) 1-1150 Me 2 HHH Br (CO _Two Et, CH _Two OEt) 1-1151 Me 2 HHH Br (CO _Two Et, CH _Two CO _Two Me) 1-1152 Me 2 HHH Br (CO _Two Et, CH _Two CO _Two Et) 1-1153 Me 2 HHH Br (CO _Two Et, CH _Two CN) 1-1154 Me 2 HHH Br (CO _Two Et, CH _Two CF _Three ) 1-1155 Me 2 HHH Br (CO _Two Et, CH _Two C≡CH) 1-1156 Me 2 HHH Br (CO _Two Et, CO _Two Et) 1-1157 Me 2 HHH Br (CO _Two Et, COCO _Two Me) 1-1158 Et 0 HHH Br (H, H) 1-1159 Et 1 HHH Br (H, H) 1-1160 Et 0 HHH Br (H, COMe) 1-1161 Et 0 HHH Br (H, COEt) 1-1162 Et 0 HHH Br (H, COPr) 1-1163 Et 0 HHH Br (H, COiPr) 1-1164 Et 0 HHH Br (H, COBu) 1-1165 Et 0 HHH Br (H, COsBu) 1- 1166 Et 0 HHH Br (H, COiBu) 1-1167 Et 0 HHH Br (H, COtBu) 1-1168 Et 0 HHH Br (H, COcPr) 1-1169 Et 0 HHH Br (H, COCH = CH _Two ) 1-1170 Et 0 HHH Br (H, COC (Me) = CH _Two ) 1-1171 Et 0 HHH Br (H, COCH = CHMe) 1-1172 Et 0 HHH Br (H, COCH = CHCl) 1-1173 Et 0 HHH Br (H, COC≡CH) 1-1174 Et 0 HHH Br (H, COCH _Two CH = CH _Two ) 1-1175 Et 0 HHH Br (H, COCH _Two C≡CH) 1-1176 Et 0 HHH Br (H, COCH _Two F) 1-1177 Et 0 HHH Br (H, COCH _Two Cl) 1-1178 Et 0 HHH Br (H, COCH _Two Br) 1-1179 Et 0 HHH Br (H, COCH _Two OMe) 1-1180 Et 0 HHH Br (H, COCH _Two OEt) 1-1181 Et 0 HHH Br (H, COCH _Two CN) 1-1182 Et 0 HHH Br (H, CH _Two CO _Two Me) 1-1183 Et 0 HHH Br (H, CH _Two CO _Two Et) 1-1184 Et 0 HHH Br (H, COCH _Two CH _Two Cl) 1-1185 Et 0 HHH Br (H, COCH _Two CH _Two OMe) 1-1186 Et 0 HHH Br (H, COCH _Two CH _Two OEt) 1-1187 Et 0 HHH Br (H, CO _Two Me) 1-1188 Et 1 HHH Br (H, CO _Two Me) 1-1189 Et 0 HHH Br (H, CO _Two Et) 1-1190 Et 1 HHH Br (H, CO _Two Et) 1-1191 Et 0 HHH Br (H, CO _Two Pr) 1-1192 Et 0 HHH Br (H, CO _Two iPr) 1-1193 Et 0 HHH Br (H, CO _Two Bu) 1-1194 Et 0 HHH Br (H, CO _Two iBu) 1-1195 Et 0 HHH Br (H, CO _Two tBu) 1-1196 Et 0 HHH Br (H, CO _Two CH _Two CH = CH _Two ) 1-1197 Et 0 HHH Br (H, CO _Two CH _Two CH _Two OMe) 1-1198 Et 0 HHH Br (H, CO _Two CH _Two CH _Two OEt) 1-1199 Et 0 HHH Br (H, CO _Two CH _Two CH _Two Cl) 1-1200 Et 0 HHH Br (H, CO _Two CH _Two CH _Two CN) 1-1201 Et 0 HHH Br (H, CO _Two CH _Two Cl) 1-1202 Et 0 HHH Br (H, CO _Two CHClCH _Three ) 1-1203 Et 0 HHH Br (H, CO _Two CH _Two CCl _Three ) 1-1204 Et 0 HHH Br (H, CO _Two CH _Two CF _Three ) 1-1205 Et 0 HHH Br (H, COCOMe) 1-1206 Et 0 HHH Br (H, COCOEt) 1-1207 Et 0 HHH Br (H, COCO _Two Me) 1-1208 Et 0 HHH Br (H, COCO _Two Et) 1-1209 Et 0 HHH Br (CO _Two (Me, Me) 1-1210 Et 0 HHH Br (CO _Two Me, Et) 1-1211 Et 0 HHH Br (CO _Two Me, Pr) 1-1212 Et 0 HHH Br (CO _Two Me, CH _Two CH = CH _Two ) 1-1213 Et 0 HHH Br (CO _Two Me, CH _Two OMe) 1-1214 Et 0 HHH Br (CO _Two Me, CH _Two OEt) 1-1215 Et 0 HHH Br (CO _Two Me, CH _Two CO _Two Me) 1-1216 Et 0 HHH Br (CO _Two Me, CH _Two CO _Two Et) 1-1217 Et 0 HHH Br (CO _Two Me, CH _Two CN) 1-1218 Et 0 HHH Br (CO _Two Me, CH _Two CF _Three ) 1-1219 Et 0 HHH Br (CO _Two Me, CH _Two C≡CH) 1-1220 Et 0 HHH Br (CO _Two Me, COMe) 1-1221 Et 0 HHH Br (CO _Two Me, COEt) 1-1222 Et 0 HHH Br (CO _Two Me, CO _Two Me) 1-1223 Et 0 HHH Br (CO _Two Me, CO _Two Et) 1-1224 Et 0 HHH Br (CO _Two Me, COCO _Two Me) 1-1225 Et 0 HHH Br (CO _Two Et, Me) 1-1226 Et 0 HHH Br (CO _Two Et, Et) 1-1227 Et 0 HHH Br (CO _Two Et, Pr) 1-1228 Et 0 HHH Br (CO _Two Et, CH _Two CH = CH _Two ) 1-1229 Et 0 HHH Br (CO _Two Et, CH _Two OMe) 1-1230 Et 0 HHH Br (CO _Two Et, CH _Two OEt) 1-1231 Et 0 HHH Br (CO _Two Et, CH _Two CO _Two Me) 1-1232 Et 0 HHH Br (CO _Two Et, CH _Two CO _Two Et) 1-1233 Et 0 HHH Br (CO _Two Et, CH _Two CN) 1-1234 Et 0 HHH Br (CO _Two Et, CH _Two CF _Three ) 1-1235 Et 0 HHH Br (CO _Two Et, CH _Two OH) 1-1236 Et 0 HHH Br (CO _Two Et, CH _Two C≡CH) 1-1237 Et 0 HHH Br (CO _Two Et, COMe) 1-1238 Et 0 HHH Br (CO _Two Et, COEt) 1-1239 Et 0 HHH Br (CO _Two Et, CO _Two Et) 1-1240 Et 0 HHH Br (CO _Two Et, COCO _Two Me) 1-1241 Et 2 HHH Br (H, H) 1-1242 Et 2 HHH Br (H, COe) 1-1243 Et 2 HHH Br (H, COEt) 1-1244 Et 2 HHH Br (H, COPr) 1-1245 Et 2 HHH Br (H, COiBu) 1-1246 Et 2 HHH Br (H, COBu) 1-1247 Et 2 HHH Br (H, COsBu) 1-1248 Et 2 HHH Br (H, COiBu) 1- 1249 Et 2 HHH Br (H, COtBu) 1-1250 Et 2 HHH Br (H, COcPr) 1-1251 Et 2 HHH Br (H, COCH = CH _Two ) 1-1252 Et 2 HHH Br (H, COCH = CHMe) 1-1253 Et 2 HHH Br (H, COCH = CHCl) 1-1254 Et 2 HHH Br (H, COC≡CH) 1-1255 Et 2 HHH Br (H, COCH _Two CH = CH _Two ) 1-1256 Et 2 HHH Br (H, COCH _Two C≡CH) 1-1257 Et 2 HHH Br (H, COCH _Two F) 1-1258 Et 2 HHH Br (H, COCH _Two Cl) 1-1259 Et 2 HHH Br (H, COCH _Two Br) 1-1260 Et 2 HHH Br (H, COCH _Two OMe) 1-1261 Et 2 HHH Br (H, COCH _Two OEt) 1-1262 Et 2 HHH Br (H, COCH _Two CN) 1-1263 Et 2 HHH Br (H, CH _Two CO _Two Me) 1-1264 Et 2 HHH Br (H, CH _Two CO _Two Et) 1-1265 Et 2 HHH Br (H, COCH _Two CH _Two Cl) 1-1266 Et 2 HHH Br (H, COCH _Two CH _Two OMe) 1-1267 Et 2 HHH Br (H, COCH ₂ CH ₂ OEt) 1-1269 Et 2 HHH Br (H, CO _Two Et) 1-1270 Et 2 HHH Br (H, CO _Two Pr) 1-1271 Et 2 HHH Br (H, CO _Two iPr) 1-1272 Et 2 HHH Br (H, CO _Two Bu) 1-1273 Et 2 HHH Br (H, CO _Two iBu) 1-1274 Et 2 HHH Br (H, CO _Two tBu) 1-1275 Et 2 HHH Br (H, CO _Two CH _Two CH = CH _Two ) 1-1276 Et 2 HHH Br (H, CO _Two CH _Two CH _Two OMe) 1-1277 Et 2 HHH Br (H, CO _Two CH _Two CH _Two OEt) 1-1278 Et 2 HHH Br (H, CO _Two CH _Two CH _Two Cl) 1-1279 Et 2 HHH Br (H, CO _Two CH _Two CH _Two CN) 1-1280 Et 2 HHH Br (H, CO _Two CH _Two Cl) 1-1281 Et 2 HHH Br (H, CO _Two CHCl _Three ) 1-1282 Et 2 HHH Br (H, CO _Two CH _Two CCl _Three ) 1-1283 Et 2 HHH Br (H, CO _Two CH _Two CF _Three ) 1-1284 Et 2 HHH Br (H, COCOe) 1-1285 Et 2 HHH Br (H, COCOEt) 1-1286 Et 2 HHH Br (H, COCOPh) 1-1287 Et 2 HHH Br (H, COCO _Two Me) 1-1288 Et 2 HHH Br (H, COCO _Two Et) 1-1289 Et 2 HHH Br (CO _Two Me, Me) 1-1290 Et 2 HHH Br (CO _Two Me, Et) 1-1291 Et 2 HHH Br (CO _Two Me, Pr) 1-1292 Et 2 HHH Br (CO _Two Me, CH _Two CH = CH _Two ) 1-1293 Et 2 HHH Br (CO _Two Me, CH _Two OMe) 1-1294 Et 2 HHH Br (CO _Two Me, CH _Two OEt) 1-1295 Et 2 HHH Br (CO _Two Me, CH _Two CO _Two Me) 1-1296 Et 2 HHH Br (CO _Two Me, CH _Two CO _Two Et) 1-1297 Et 2 HHH Br (CO _Two Me, CH _Two CN) 1-1298 Et 2 HHH Br (CO _Two Me, CH _Two CF _Three ) 1-1299 Et 2 HHH Br (CO _Two Me, CH _Two C≡CH) 1-1300 Et 2 HHH Br (CO _Two Me, COMe) 1-1301 Et 2 HHH Br (CO _Two Me, COEt) 1-1302 Et 2 HHH Br (CO _Two Me, CO _Two Me) 1-1303 Et 2 HHH Br (CO _Two Me, CO _Two Et) 1-1304 Et 2 HHH Br (CO _Two Me, COCO _Two Me) 1-1305 Et 2 HHH Br (CO _Two Et, Me) 1-1306 Et 2 HHH Br (CO _Two Et, Et) 1-1307 Et 2 HHH Br (CO _Two Et, Pr) 1-1308 Et 2 HHH Br (CO _Two Et, CH _Two CH = CH _Two ) 1-1309 Et 2 HHH Br (CO _Two Et, CH _Two OMe) 1-1310 Et 2 HHH Br (CO _Two Et, CH _Two OEt) 1-1311 Et 2 HHH Br (CO _Two Et, CH _Two CO _Two Me) 1-1312 Et 2 HHH Br (CO _Two Et, CH _Two CO _Two Et) 1-1313 Et 2 HHH Br (CO _Two Et, CH _Two CN) 1-1314 Et 2 HHH Br (CO _Two Et, CH _Two CF _Three ) 1-1315 Et 2 HHH Br (CO _Two Et, CH _Two C≡CH) 1-1316 Et 2 HHH Br (CO _Two Et, COMe) 1-1317 Et 2 HHH Br (CO _Two Et, COEt) 1-1318 Et 2 HHH Br (CO _Two Et, CO _Two Et) 1-1319 Et 2 HHH Br (CO _Two Et, COCO _Two Me) 1-1320 Pr 0 HHH Br (H, H) 1-1321 Pr 0 HHH Br (H, COMe) 1-1322 Pr 0 HHH Br (H, COEt) 1-1323 Pr 0 HHH Br (H, CO _Two Me) 1-1324 Pr 0 HHH Br (H, CO _Two Et) 1-1325 iPr 0 HHH Br (H, H) 1-1326 iPr 0 HHH Br (H, COet) 1-1327 iPr 0 HHH Br (H, COEt) 1-1328 iPr 0 HHH Br (H, CO _Two Me) 1-1329 iPr 0 HHH Br (H, CO _Two Et) 1-1330 CH _Two CH = CH _Two 0 HHH Br (H, H) 1-1331 CH _Two CH = CH _Two 0 HHH Br (H, CO _Two Me) 1-1332 CH _Two CH = CH _Two 0 HHH Br (H, CO _Two Et) 1-1501 Me 0 HHHF (H, H) 1-1502 Me 0 HHHF (H, COMe) 1-1503 Me 0 HHHF (H, COEt) 1-1504 Me 0 HHHF (H, COPr) 1-1505 Me 0 HHHF (H, COiPr) 1-1506 Me 0 HHHF (H, COBu) 1-1507 Me 0 HHHF (H, COsBu) 1-1508 Me 0 HHHF (H, COiBu) 1-1509 Me 0 HHHF (H, COtBu) ) 1-1510 Me 0 HHHF (H, COcPr) 1-1511 Me 0 HHHF (H, COCH = CH _Two ) 1-1512 Me 0 HHHF (H, COCH = CHMe) 1-1513 Me 0 HHHF (H, COCH = CHCl) 1-1514 Me 0 HHHF (H, COC≡CH) 1-1515 Me 0 HHHF (H, COC (≡CMe) 1-1516 Me 0 HHHF (H, COCH _Two CH = CH _Two ) 1-1517 Me 0 HHHF (H, COCH _Two C≡CH) 1-1518 Me 0 HHHF (H, COCH _Two F) 1-1519 Me 0 HHHF (H, COCH _Two Cl) 1-1520 Me 0 HHHF (H, COCH _Two Br) 1-1521 Me 0 HHHF (H, COCH _Two OMe) 1-1522 Me 0 HHHF (H, COCH _Two OEt) 1-1525 Me 0 HHHF (H, COCH _Two CN) 1-1526 Me 0 HHHF (H, CH _Two CO _Two Me) 1-1527 Me 0 HHHF (H, CH _Two CO _Two Et) 1-1528 Me 0 HHHF (H, COCH _Two CH _Two Cl) 1-1529 Me 0 HHHF (H, COCH _Two CH _Two OMe) 1-1530 Me 0 HHHF (H, COCH _Two CH _Two OEt) 1-1531 Me 0 HHHF (H, CO _Two Me) 1-1532 Me 1 HHHF (H, CO _Two Me) 1-1533 Me 0 HHHF (H, CO _Two Et) 1-1534 Me 1 HHHF (H, CO _Two Et) 1-1535 Me 0 HHHF (H, CO _Two Pr) 1-1536 Me 0 HHHF (H, CO _Two iPr) 1-1537 Me 0 HHHF (H, CO _Two Bu) 1-1538 Me 0 HHHF (H, CO _Two iBu) 1-1539 Me 0 HHHF (H, CO _Two tBu) 1-1540 Me 0 HHHF (H, CO _Two CH _Two CH = CH _Two ) 1-1541 Me 0 HHHF (H, CO _Two CH _Two CH _Two OMe) 1-1542 Me 0 HHHF (H, CO _Two CH _Two CH _Two OEt) 1-1543 Me 0 HHHF (H, CO _Two CH _Two CH _Two Cl) 1-1544 Me 0 HHHF (H, CO _Two CH _Two CH _Two CN) 1-1545 Me 0 HHHF (H, CO _Two CH _Two Cl) 1-1546 Me 0 HHHF (H, CO _Two CHClMe) 1-1547 Me 0 HHHF (H, CO _Two CH _Two CCl _Three ) 1-1548 Me 0 HHHF (H, CO _Two CH _Two CF _Three ) 1-1549 Me 0 HHHF (H, COCOMe) 1-1550 Me 0 HHHF (H, COCOEt) 1-1551 Me 0 HHHF (H, COCO _Two Me) 1-1552 Me 0 HHHF (H, COCO _Two Et) 1-1553 Me 0 HHHF (CO _Two Me, Me) 1-1554 Me 0 HHHF (CO _Two Me, Et) 1-1555 Me 0 HHHF (CO _Two Me, Pr) 1-1556 Me 0 HHHF (CO _Two Me, CH _Two CH = CH _Two ) 1-1557 Me 0 HHHF (CO _Two Me, CH _Two OMe) 1-1558 Me 0 HHHF (CO _Two Me, CH _Two OEt) 1-1559 Me 0 HHHF (CO _Two Me, CH _Two CO _Two Me) 1-1560 Me 0 HHHF (CO _Two Me, CH _Two CO _Two Et) 1-1561 Me 0 HHHF (CO _Two Me, CH _Two CN) 1-1562 Me 0 HHHF (CO _Two Me, CH _Two CF _Three ) 1-1563 Me 0 HHHF (CO _Two Me, CH _Two C≡CH) 1-1564 Me 0 HHHF (CO _Two Me, COMe) 1-1565 Me 0 HHHF (CO _Two Me, COEt) 1-1566 Me 0 HHHF (CO _Two Me, CO _Two Me) 1-1567 Me 0 HHHF (CO _Two Me, CO _Two Et) 1-1568 Me 0 HHHF (CO _Two Me, COCO _Two Me) 1-1569 Me 0 HHHF (CO _Two Et, Me) 1-1570 Me 0 HHHF (CO _Two Et, Et) 1-1571 Me 0 HHHF (CO _Two Et, Pr) 1-1572 Me 0 HHHF (CO _Two Et, CH _Two CH = CH _Two ) 1-1573 Me 0 HHHF (CO _Two Et, CH _Two OMe) 1-1574 Me 0 HHHF (CO _Two Et, CH _Two OEt) 1-1575 Me 0 HHHF (CO _Two Et, CH _Two CO _Two Me) 1-1576 Me 0 HHHF (CO _Two Et, CH _Two CO _Two Et) 1-1577 Me 0 HHHF (CO _Two Et, CH _Two CN) 1-1578 Me 0 HHHF (CO _Two Et, CH _Two CF _Three ) 1-1579 Me 0 HHHF (CO _Two Et, CH _Two C≡CH) 1-1580 Me 0 HHHF (CO _Two Et, CO _Two Et) 1-1581 Me 0 HHHF (CO _Two Et, COCO _Two Me) 1-1582 Me 2 HHHF (H, H) 1-1583 Me 2 HHHF (H, COMe) 1-1584 Me 2 HHHF (H, COEt) 1-1585 Me 2 HHHF (H, COPr) 1-1586 Me 2 HHHF (H, COiPr) 1-1587 Me 2 HHHF (H, COBu) 1-1588 Me 2 HHHF (H, COsBu) 1-1589 Me 2 HHHF (H, COiBu) 1-1590 Me 2 HHHF (H, COtBu) ) 1-1591 Me 2 HHHF (H, COcPr) 1-1592 Me 2 HHHF (H, COCH = CH _Two ) 1-1593 Me 2 HHHF (H, COCH = CHMe) 1-1594 Me 2 HHHF (H, COCH = CHCl) 1-1595 Me 2 HHHF (H, COC≡CH) 1-1596 Me 2 HHHF (H, COCH _Two CH = CH _Two ) 1-1597 Me 2 HHHF (H, COCH _Two C≡CH) 1-1598 Me 2 HHHF (H, COCH _Two F) 1-1599 Me 2 HHHF (H, COCH _Two Cl) 1-1600 Me 2 HHHF (H, COCH _Two Br) 1-1601 Me 2 HHHF (H, COCH _Two OMe) 1-1602 Me 2 HHHF (H, COCH _Two OEt) 1-1603 Me 2 HHHF (H, COCH _Two CN) 1-1604 Me 2 HHHF (H, CH _Two CO _Two Me) 1-1605 Me 2 HHHF (H, CH _Two CO _Two Et) 1-1606 Me 2 HHHF (H, COCH _Two CH _Two Cl) 1-1607 Me 2 HHHF (H, COCH _Two CH _Two OMe) 1-1608 Me 2 HHHF (H, COCH _Two CH _Two OEt) 1-1609 Me 2 HHHF (H, CO _Two Me) 1-1610 Me 2 HHHF (H, CO _Two Et) 1-1611 Me 2 HHHF (H, CO _Two Pr) 1-1612 Me 2 HHHF (H, CO _Two iPr) 1-1613 Me 2 HHHF (H, CO _Two Bu) 1-1614 Me 2 HHHF (H, CO _Two iBu) 1-1615 Me 2 HHHF (H, CO _Two tBu) 1-1616 Me 2 HHHF (H, CO _Two CH _Two CH = CH _Two ) 1-1617 Me 2 HHHF (H, CO _Two CH _Two CH _Two OMe) 1-1618 Me 2 HHHF (H, CO _Two CH _Two CH _Two OEt) 1-1619 Me 2 HHHF (H, CO _Two CH _Two CH _Two Cl) 1-1620 Me 2 HHHF (H, CO _Two CH _Two CH _Two CN) 1-1621 Me 2 HHHF (H, CO _Two CH _Two Cl) 1-1622 Me 2 HHHF (H, CO _Two CHCl _Three ) 1-1623 Me 2 HHHF (H, CO _Two CH _Two CCl _Three ) 1-1624 Me 2 HHHF (H, CO _Two CH _Two CF _Three ) 1-1625 Me 2 HHHF (H, COCOe) 1-1626 Me 2 HHHF (H, COCOEt) 1-1627 Me 2 HHHF (H, COCOe) _Two Me) 1-1628 Me 2 HHHF (H, COCO _Two Et) 1-1629 Me 2 HHHF (CO _Two Me, Me) 1-1630 Me 2 HHHF (CO _Two Me, Et) 1-1631 Me 2 HHHF (CO _Two Me, Pr) 1-1632 Me 2 HHHF (CO _Two Me, CH _Two CH = CH _Two ) 1-1633 Me 2 HHHF (CO _Two Me, CH _Two OMe) 1-1634 Me 2 HHHF (CO _Two Me, CH _Two OEt) 1-1635 Me 2 HHHF (CO _Two Me, CH _Two CO _Two Me) 1-1636 Me 2 HHHF (CO _Two Me, CH _Two CO _Two Et) 1-1637 Me 2 HHHF (CO _Two Me, CH _Two CN) 1-1638 Me 2 HHHF (CO _Two Me, CH _Two CF _Three ) 1-1639 Me 2 HHHF (CO _Two Me, CH _Two C≡CH) 1-1640 Me 2 HHHF (CO ₂ Me, COMe) 1-1642 Me 2 HHHF (CO _Two Me, CO _Two Me) 1-1643 Me 2 HHHF (CO _Two Me, CO _Two Et) 1-1644 Me 2 HHHF (CO _Two Me, COCO _Two Me) 1-1645 Me 2 HHHF (CO _Two Et, Me) 1-1646 Me 2 HHHF (CO _Two Et, Et) 1-1647 Me 2 HHHF (CO _Two Et, Pr) 1-1648 Me 2 HHHF (CO _Two Et, CH _Two CH = CH _Two ) 1-1649 Me 2 HHHF (CO _Two Et, CH _Two OMe) 1-1650 Me 2 HHHF (CO _Two Et, CH _Two OEt) 1-1651 Me 2 HHHF (CO _Two Et, CH _Two CO _Two Me) 1-1652 Me 2 HHHF (CO _Two Et, CH _Two CO _Two Et) 1-1653 Me 2 HHHF (CO _Two Et, CH _Two CN) 1-1654 Me 2 HHHF (CO _Two Et, CH _Two CF _Three ) 1-1655 Me 2 HHHF (CO _Two Et, CH _Two C≡CH) 1-1656 Me 2 HHHF (CO _Two Et, CO _Two Et) 1-1657 Me 2 HHHF (CO _Two Et, COCO _Two Me) 1-1658 Et 0 HHHF (H, H) 1-1659 Et 1 HHHF (H, H) 1-1660 Et 0 HHHF (H, COMe) 1-1661 Et 0 HHHF (H, COEt) 1-1662 Et 0 HHHF (H, COPr) 1-1663 Et 0 HHHF (H, COiPr) 1-1664 Et 0 HHHF (H, COBu) 1-1665 Et 0 HHHF (H, COsBu) 1-1666 Et 0 HHHF (H, COiBu ) 1-1667 Et 0 HHHF (H, COtBu) 1-1668 Et 0 HHHF (H, COcPr) 1-1669 Et 0 HHHF (H, COCH = CH _Two ) 1-1670 Et 0 HHHF (H, COC (Me) = CH _Two ) 1-1671 Et 0 HHHF (H, COCH = CHMe) 1-1672 Et 0 HHHF (H, COCH = CHCl) 1-1673 Et 0 HHHF (H, COC≡CH) 1-1674 Et 0 HHHF (H, COCH _Two CH = CH _Two ) 1-1675 Et 0 HHHF (H, COCH _Two C≡CH) 1-1676 Et 0 HHHF (H, COCH _Two F) 1-1677 Et 0 HHHF (H, COCH _Two Cl) 1-1678 Et 0 HHHF (H, COCH _Two Br) 1-1679 Et 0 HHHF (H, COCH _Two OMe) 1-1680 Et 0 HHHF (H, COCH _Two OEt) 1-1681 Et 0 HHHF (H, COCH _Two CN) 1-1682 Et 0 HHHF (H, CH _Two CO _Two Me) 1-1683 Et 0 HHHF (H, CH _Two CO _Two Et) 1-1684 Et 0 HHHF (H, COCH _Two CH _Two Cl) 1-1685 Et 0 HHHF (H, COCH _Two CH _Two OMe) 1-1686 Et 0 HHHF (H, COCH _Two CH _Two OEt) 1-1687 Et 0 HHHF (H, CO _Two Me) 1-1688 Et 1 HHHF (H, CO _Two Me) 1-1689 Et 0 HHHF (H, CO _Two Et) 1-1690 Et 1 HHHF (H, CO _Two Et) 1-1691 Et 0 HHHF (H, CO _Two Pr) 1-1692 Et 0 HHHF (H, CO _Two iPr) 1-1693 Et 0 HHHF (H, CO _Two Bu) 1-1694 Et 0 HHHF (H, CO _Two iBu) 1-1695 Et 0 HHHF (H, CO _Two tBu) 1-1696 Et 0 HHHF (H, CO _Two CH _Two CH = CH _Two ) 1-1697 Et 0 HHHF (H, CO _Two CH _Two CH _Two OMe) 1-1698 Et 0 HHHF (H, CO _Two CH _Two CH _Two OEt) 1-1699 Et 0 HHHF (H, CO _Two CH _Two CH _Two Cl) 1-1700 Et 0 HHHF (H, CO _Two CH _Two CH _Two CN) 1-1701 Et 0 HHHF (H, CO _Two CH _Two Cl) 1-1702 Et 0 HHHF (H, CO _Two CHClCH _Three ) 1-1703 Et 0 HHHF (H, CO _Two CH _Two CCl _Three ) 1-1704 Et 0 HHHF (H, CO _Two CH _Two CF _Three ) 1-1705 Et 0 HHHF (H, COCOMe) 1-1706 Et 0 HHHF (H, COCOEt) 1-1707 Et 0 HHHF (H, COCO _Two Me) 1-1708 Et 0 HHHF (H, COCO _Two Et) 1-1709 Et 0 HHHF (CO _Two Me, Me) 1-1710 Et 0 HHHF (CO _Two Me, Et) 1-1711 Et 0 HHHF (CO _Two Me, Pr) 1-1712 Et 0 HHHF (CO _Two Me, CH _Two CH = CH _Two ) 1-1713 Et 0 HHHF (CO _Two Me, CH _Two OMe) 1-1714 Et 0 HHHF (CO _Two Me, CH _Two OEt) 1-1715 Et 0 HHHF (CO _Two Me, CH _Two CO _Two Me) 1-1716 Et 0 HHHF (CO _Two Me, CH _Two CO _Two Et) 1-1717 Et 0 HHHF (CO _Two Me, CH _Two CN) 1-1718 Et 0 HHHF (CO _Two Me, CH _Two CF _Three ) 1-1719 Et 0 HHHF (CO _Two Me, CH _Two C≡CH) 1-1720 Et 0 HHHF (CO _Two Me, COMe) 1-1721 Et 0 HHHF (CO _Two Me, COEt) 1-1722 Et 0 HHHF (CO _Two Me, CO _Two Me) 1-1723 Et 0 HHHF (CO _Two Me, CO _Two Et) 1-1724 Et 0 HHHF (CO _Two Me, COCO _Two Me) 1-1725 Et 0 HHHF (CO _Two Et, Me) 1-1726 Et 0 HHHF (CO _Two Et, Et) 1-1727 Et 0 HHHF (CO _Two Et, Pr) 1-1728 Et 0 HHHF (CO _Two Et, CH _Two CH = CH _Two ) 1-1729 Et 0 HHHF (CO _Two Et, CH _Two OMe) 1-1730 Et 0 HHHF (CO _Two Et, CH _Two OEt) 1-1731 Et 0 HHHF (CO _Two Et, CH _Two CO _Two Me) 1-1732 Et 0 HHHF (CO _Two Et, CH _Two CO _Two Et) 1-1733 Et 0 HHHF (CO _Two Et, CH _Two CN) 1-1734 Et 0 HHHF (CO _Two Et, CH _Two CF _Three ) 1-1735 Et 0 HHHF (CO _Two Et, CH _Two OH) 1-1736 Et 0 HHHF (CO _Two Et, CH _Two C≡CH) 1-1737 Et 0 HHHF (CO _Two Et, COMe) 1-1738 Et 0 HHHF (CO _Two Et, COEt) 1-1739 Et 0 HHHF (CO _Two Et, CO _Two Et) 1-1740 Et 0 HHHF (CO _Two Et, COCO _Two Me) 1-1741 Et 2 HHHF (H, H) 1-1742 Et 2 HHHF (H, COMe) 1-1743 Et 2 HHHF (H, COEt) 1-1744 Et 2 HHHF (H, COPr) 1-1745 Et 2 HHHF (H, COiPr) 1-1746 Et 2 HHHF (H, COBu) 1-1747 Et 2 HHHF (H, COsBu) 1-1748 Et 2 HHHF (H, COiBu) 1-1749 Et 2 HHHF (H, COtBu) ) 1-1750 Et 2 HHHF (H, COcPr) 1-1751 Et 2 HHHF (H, COCH = CH _Two ) 1-1752 Et 2 HHHF (H, COCH = CHMe) 1-1753 Et 2 HHHF (H, COCH = CHCl) 1-1754 Et 2 HHHF (H, COC≡CH) 1-1755 Et 2 HHHF (H, COCH _Two CH = CH _Two ) 1-1756 Et 2 HHHF (H, COCH _Two C≡CH) 1-1757 Et 2 HHHF (H, COCH _Two F) 1-1758 Et 2 HHHF (H, COCH _Two Cl) 1-1759 Et 2 HHHF (H, COCH _Two Br) 1-1760 Et 2 HHHF (H, COCH _Two OMe) 1-1761 Et 2 HHHF (H, COCH _Two OEt) 1-1762 Et 2 HHHF (H, COCH _Two CN) 1-1763 Et 2 HHHF (H, CH _Two CO _Two Me) 1-1764 Et 2 HHHF (H, CH _Two CO _Two Et) 1-1765 Et 2 HHHF (H, COCH _Two CH _Two Cl) 1-1766 Et 2 HHHF (H, COCH _Two CH _Two OMe) 1-1767 Et 2 HHHF (H, COCH _Two CH _Two OEt) 1-1768 Et 2 HHHF (H, CO _Two Me) 1-1769 Et 2 HHHF (H, CO _Two Et) 1-1770 Et 2 HHHF (H, CO _Two Pr) 1-1771 Et 2 HHHF (H, CO _Two iPr) 1-1772 Et 2 HHHF (H, CO _Two Bu) 1-1773 Et 2 HHHF (H, CO _Two iBu) 1-1774 Et 2 HHHF (H, CO _Two tBu) 1-1775 Et 2 HHHF (H, CO _Two CH _Two CH = CH _Two ) 1-1776 Et 2 HHHF (H, CO _Two CH _Two CH _Two OMe) 1-1777 Et 2 HHHF (H, CO _Two CH _Two CH _Two OEt) 1-1778 Et 2 HHHF (H, CO _Two CH _Two CH _Two Cl) 1-1779 Et 2 HHHF (H, CO _Two CH _Two CH _Two CN) 1-1780 Et 2 HHHF (H, CO _Two CH _Two Cl) 1-1781 Et 2 HHHF (H, CO _Two CHCl _Three ) 1-1782 Et 2 HHHF (H, CO _Two CH _Two CCl _Three ) 1-1783 Et 2 HHHF (H, CO _Two CH _Two CF _Three ) 1-1784 Et 2 HHHF (H, COCOMe) 1-1785 Et 2 HHHF (H, COCOEt) 1-1786 Et 2 HHHF (H, COCOPh) 1-1787 Et 2 HHHF (H, COCO _Two Me) 1-1788 Et 2 HHHF (H, COCO _Two Et) 1-1789 Et 2 HHHF (CO _Two (Me, Me) 1-1790 Et 2 HHHF (CO _Two Me, Et) 1-1791 Et 2 HHHF (CO _Two Me, Pr) 1-1792 Et 2 HHHF (CO _Two Me, CH _Two CH = CH _Two ) 1-1793 Et 2 HHHF (CO _Two Me, CH _Two OMe) 1-1794 Et 2 HHHF (CO _Two Me, CH _Two OEt) 1-1795 Et 2 HHHF (CO _Two Me, CH _Two CO _Two Me) 1-1796 Et 2 HHHF (CO _Two Me, CH _Two CO _Two Et) 1-1797 Et 2 HHHF (CO _Two Me, CH _Two CN) 1-1798 Et 2 HHHF (CO _Two Me, CH _Two CF _Three ) 1-1799 Et 2 HHHF (CO _Two Me, CH _Two C≡CH) 1-1800 Et 2 HHHF (CO _Two Me, COMe) 1-1801 Et 2 HHHF (CO _Two Me, COEt) 1-1802 Et 2 HHHF (CO _Two Me, CO _Two Me) 1-1803 Et 2 HHHF (CO _Two Me, CO _Two Et) 1-1804 Et 2 HHHF (CO _Two Me, COCO _Two Me) 1-1805 Et 2 HHHF (CO _Two Et, Me) 1-1806 Et 2 HHHF (CO _Two Et, Et) 1-1807 Et 2 HHHF (CO _Two Et, Pr) 1-1808 Et 2 HHHF (CO _Two Et, CH _Two CH = CH _Two ) 1-1809 Et 2 HHHF (CO _Two Et, CH _Two OMe) 1-1810 Et 2 HHHF (CO _Two Et, CH _Two OEt) 1-1811 Et 2 HHHF (CO _Two Et, CH _Two CO _Two Me) 1-1812 Et 2 HHHF (CO _Two Et, CH _Two CO _Two Et) 1-1813 Et 2 HHHF (CO _Two Et, CH _Two CN) 1-1814 Et 2 HHHF (CO _Two Et, CH _Two CF _Three ) 1-1815 Et 2 HHHF (CO _Two Et, CH _Two C≡CH) 1-1816 Et 2 HHHF (CO _Two Et, COMe) 1-1817 Et 2 HHHF (CO _Two Et, COEt) 1-1818 Et 2 HHHF (CO _Two Et, CO _Two Et) 1-1819 Et 2 HHHF (CO _Two Et, COCO _Two Me) 1-1820 Pr 0 HHHF (H, H) 1-1821 Pr 0 HHHF (H, COMe) 1-1822 Pr 0 HHHF (H, COEt) 1-1823 Pr 0 HHHF (H, CO _Two Me) 1-1824 Pr 0 HHHF (H, CO _Two Et) 1-1825 iPr 0 HHHF (H, H) 1-1826 iPr 0 HHHF (H, COMe) 1-1827 iPr 0 HHHF (H, COEt) 1-1828 iPr 0 HHHF (H, CO _Two Me) 1-1829 iPr 0 HHHF (H, CO _Two Et) 1-1830 CH _Two CH = CH _Two 0 HHHF (H, H) 1-1831 CH _Two CH = CH _Two 0 HHHF (H, CO _Two Me) 1-1832 CH _Two CH = CH _Two 0 HHHF (H, CO _Two Et) 1-1833 Et 0 HHH Cl (Me, COMe) 1-1834 Et 0 Me HH Cl (H, CO _Two Et) 1-1835 Et 0 HHH CO _Two Me (H, CO _Two Et) 1-1836 Et 0 HHH CONHCH _Two CF _Three (H, CO _Two Et) 1-1837 Et 0 HHH OMe (H, CO _Two Et) 1-1838 Et 1 HHH OMe (H, CO _Two Et) 1-1839 Et 0 HHH Me (H, CO _Two Et) 1-1840 Et 1 HHH Me (H, CO _Two Et) 1-1841 Et 0 HHH CF _Three (H, CO _Two Et) 1-1842 Et 1 HHH CF _Three (H, CO _Two Et) 1-1843 Et 0 HHH OCF _Three (H, CO _Two Et) 1-1844 Et 1 HHH OCF _Three (H, CO _Two Et) 1-1845 Et 0 HHH Cl (H, CO-5- (1,4-Me _Two -Pyza) 1-1846 Et 0 HHH Cl (H, Furo) 1-1847 Et 0 HHH Cl (H, 2-CO _Two H-Bz) 1-1848 Et 0 HHH Cl (H, COCH _Two CH _Two CO _Two H) 1-1849 Et 0 HHH Cl (H, CONHCO _Two Et) 1-1850 Et 0 HHH Cl (H, CONHCH _Two CO _Two Et) 1-1851 Et 0 HHH Cl (H, COCH = CHCO _Two Et-trans) 1-1852 Et 0 HHH Cl (H, COCH = CHCO _Two Et-cis) 1-1853 Et 0 HHH Cl (Phtl) 1-1854 Et 0 HHH Cl (COCH _Two CH _Two CO) 1-1855 Et 0 HHH Cl (COCH = CHCO) 1-1856 Et 0 HHH Cl (= CHMe) 1-1857 Et 0 HHH Cl (= C (Cl) Me) 1-1858 Et 0 HHH Cl (= CMe _Two ) 1-1859 Et 0 HHH Cl (= CHNHCH _Two CH _Two OEt) 1-1860 Et 0 HHH Cl (= CHNMe _Two ) 1-1861 Et 0 HHH Cl (= CHNHCH _Two CH _Two OMe) 1-1862 Et 0 HHH Cl (= CHNHCH _Two CH _Two CH _Two OMe) ───────────────────────────────────

[0076]

[Table 2]

[0077]

Embedded image ─────────────────────────────────── Compound No.R ¹ n R ² R ³ Y _p X (R ⁴ , R ⁵ ) ─────────────────────────────────── 2-1 Me 0 HHH Cl (H, Me ) 2-2 Me 0 HHH Cl (H, COMe) 2-3 Me 0 HHH Cl (H, COEt) 2-4 Me 0 HHH Cl (H, CO ₂ Me) 2-5 Me 0 HHH Cl (H, CO ₂ Et) 2-6 Et 0 HHH Cl (H, Me) 2-7 Et 0 HHH Cl (H, COMe) 2-8 Et 0 HHH Cl (H, COEt) 2-9 Et 0 HHH Cl (H, CO ₂ Me) 2-10 Et 0 HHH Cl (H, CO ₂ Et) ───────────────────────────────── ──

[0078]

[Table 3]

[0079]

Embedded image 化合物 Compound number R ¹ n R ² R ³ Y _p X ─── ──────────────────────────────── 3-1 Me 0 HHH Cl 3-2 Me 1 HHH Cl 3-3 Me 2 HHH Cl 3-4 Et 0 HHH Cl 3-5 Et 1 HHH Cl 3-6 Et 2 HHH Cl 3-7 CF ₃ 0 HHH Cl 3-8 CF ₃ 2 HHH Cl 3-9 CH ₂ CF ₃ 0 HHH Cl 3-10 CH ₂ CF ₃ 2 HHH Cl 3-11 CF ₂ CF ₃ 0 HHH Cl 3-12 CF ₂ CF ₃ 2 HHH Cl 3-13 Pr 0 HHH Cl 3-14 Pr 2 HHH Cl 3-15 iPr 0 HHH Cl 3-16 iPr 2 HHH Cl 3-17 Bu 0 HHH Cl 3-18 Bu 2 HHH Cl 3-19 tBu 0 HHH Cl 3-20 tBu 2 HHH Cl 3-21 Me 0 HH 4-Cl Cl 3-22 Me 2 HH 4-Cl Cl 3-23 Et 0 HH 4-Cl Cl 3-24 Et 2 HH 4-Cl Cl 3-25 Me 0 HH 4-Br Cl 3-26 Me 2 HH 4-Br Cl 3-27 Et 0 HH 4-Br Cl 3-28 Et 2 HH 4-Br Cl 3-29 Me 0 HH 4-CN Cl 3-30 Me 2 HH 4-CN Cl 3-31 Et 0 HH 4-CN Cl 3-32 Et 2 HH 4-CN Cl 3-33 Me 0 HH 4-CF ₃ Cl 3-34 Me 2 HH 4-CF ₃ Cl 3-35 Et 0 HH 4-CF ₃ Cl 3-36 Et 2 HH 4-CF ₃ Cl 3-37 Et 0 HH 4-I Cl 3-38 Et 2 HH 4-I Cl 3 -39 Et 0 HH 4-MeO Cl 3-40 Et 2 HH 4-MeO Cl 3-41 CH ₂ CH = CH ₂ 0 HHH Cl 3-42 CH ₂ CH = CH ₂ 2 HHH Cl ─────── ────────────────────────────

[0080]

[Table 4]

[0081]

Embedded image 化合物 Compound number R ¹ n R ² R ³ Y _p X ─── ──────────────────────────────── 4-1 Me 0 HHH Cl 4-2 Me 2 HHH Cl 4-3 Et 0 HHH Cl 4-4 Et 2 HHH Cl ───────────────────────────────────

[0082]

[Table 5]

[0083]

Embedded image 化合物 Compound number R ¹ n R ² R ³ Y _p Xm (R ⁴ , R ⁵ ) ─────────────────────────────────── 5-1 Et 0 HHH 3,5-Cl ₂ (H, CO ₂ Et) 5-2 Et 0 HHH 3,5-Cl ₂ (H, CO ₂ Et) 5-3 Et 0 HHH 2,4-F ₂ (H, CO ₂ Et) 5-4 Et 0 HHH 3,4-F ₂ (H, CO ₂ Et) ─────────────────────────────────── Among the above exemplified compounds, preferred are 1-1, 1 and 1,
-2, 1-3, 1-4, 1-5, 1-6, 1-13, 1
-15, 1-16, 1-17, 1-18, 1-19, 1
-20, 1-31, 1-33, 1-37, 1-41, 1
-44, 1-46, 1-48, 1-50, 1-51, 1
-56, 1-57, 1-58, 1-60, 1-62, 1
-63, 1-65, 1-68, 1-73, 1-88, 1
-101, 1-104, 1-131, 1-145, 1-
146, 1-147, 1-148, 1-157, 1-1
60, 1-162, 1-163, 1-164, 1-17
4, 1-184, 1-188, 1-189, 1-19
9, 1-200, 1-201, 1-204, 1-20
6, 1-207, 1-208, 1-209, 1-22
9, 1-232, 1-233, 1-242, 1-28
8, 1-290, 1-291, 1-292, 1-29
3,1-294,1-303,1-304,1-30
6, 1-307, 1-308, 1-309, 1-31
4,1-319,1-321,1-333,1-33
4,1-336,1-339,1-344,1-34
5,1-346,1-348,1-351,1-35
3,1-354,1-356,1-360,1-37
3, 1-376, 1-379, 1-384, 1-40
1, 1-403, 1-404, 1-409, 1-41
0, 1-437, 1-438, 1-439, 1-44
0, 1-447, 1-449, 1-452, 1-45
3, 1-455, 1-457, 1-466, 1-46
8,1-476,1-479,1-481,1-48
4, 1-486, 1-491, 1-493, 1-49
5, 1-496, 1-498, 1-499, 1-50
1,1-518,1-521,1-527,1-57
9, 1-582, 1-584, 1-587, 1-60
2, 1-612, 1-622, 1-632, 1-653
And the compounds of Nos. 2 to 9 are more preferable. 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone hydrazone (Compound No. 1-1), 4-chlorophenyl = 5 -Methylthiomethylthiophen-2-yl = ketone = N-acetylhydrazone (Compound No. 1-2), 4-chlorophenyl =
5-methylthiomethylthiophen-2-yl = ketone =
N-propionylhydrazone (Compound No. 1-3), 4
-Chlorophenyl = 5-methylthiomethylthiophene-
2-yl = ketone = N-butyrylhydrazone (compound No. 1-4), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-isobutyrylhydrazone (compound No. 1-5), 4 -Chlorophenyl =
5-methylthiomethylthiophen-2-yl = ketone =
N-valerylhydrazone (Compound No. 1-6), 4-chlorophenyl = 5-methylthiomethylthiophene-2-
Il = ketone = N-cyclopropylcarbonylhydrazone (Compound No. 1-16), 4-chlorophenyl = 5-
Methylthiomethylthiophen-2-yl = ketone = N-
Cyclopentylhydrazone (Compound No. 1-18), 4
-Chlorophenyl = 5-methylthiomethylthiophene-
2-yl = ketone = N-cyclohexylhydrazone (Compound No. 1-19), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-methoxyacetylhydrazone (Compound No. 1-31), 4 -Chlorophenyl = 5-methylthiomethylthiophen-2-
Il = ketone = N- (2-methylthioethylcarbonyl) hydrazone (Compound No. 1-44), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl =
Ketone = N- (pyridinecarbo-2-yl) hydrazone (Compound No. 1-48), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-56),
4-chlorophenyl = 5-methylsulfinylmethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-57), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-ethoxycarbonyl Hydrazone (Compound No. 1
-58), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-propoxycarbonylhydrazone (Compound No. 1-60), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl =
Ketone = N-butoxycarbonylhydrazone (Compound No. 1-62), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N- (isobutoxycarbonyl) hydrazone (Compound No. 1-63), 4
-Chlorophenyl = 5-methylthiomethylthiophene-
2-yl = ketone = N- (allyloxycarbonyl) hydrazone (Compound No. 1-65), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N- (2-chloroethoxycarbonyl) hydrazone (compound No. 1-68), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-methylaminocarbonylhydrazone (Compound No. 1-8)
8), 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-131), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = hydrazone (Compound No. 1-145), 4-
Chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N-acetylhydrazone (Compound No. 1-146), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N-
Propionyl hydrazone (Compound No. 1-147), 4
-Chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N-butyrylhydrazone (compound No. 1-148), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N
-Benzoylhydrazone (compound number 1-188), 4
-Chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N- (4-chlorobenzoyl) hydrazone (Compound No. 1-189), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2
-Yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-199), 4-chlorophenyl = 5-
Methylsulfonylmethylthiophen-2-yl = ketone = N-ethoxycarbonylhydrazone (Compound No. 1-
200), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N- (propoxycarbonyl) hydrazone (Compound No. 1-201),
4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N- (isopropoxycarbonyl) hydrazone (Compound No. 1-204), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl = ketone = N-allyloxycarbonylhydrazone (Compound No. 1-206), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl =
Ketone = N- (2-methoxyethoxycarbonyl) hydrazone (Compound No. 1-207), 4-chlorophenyl = 5-methylsulfonylmethylthiophen-2-yl =
Ketone = N- (2-chloroethoxycarbonyl) hydrazone (Compound No. 1-209), 4-chlorophenyl =
5-ethylthiomethylthiophen-2-yl = ketone =
Hydrazone (Compound No. 1-288), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-acetylhydrazone (Compound No. 1-29)
0), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-propionylhydrazone (Compound No. 1-291), 4-chlorophenyl = 5
-Ethylthiomethylthiophen-2-yl = ketone = N
-Butyrylhydrazone (Compound No. 1-292), 4-
Chlorophenyl = 5-ethylthiomethylthiophene-2
-Yl = ketone = N-isobutyrylhydrazone (Compound No. 1-293), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-valerylhydrazone (Compound No. 1-294), 4 -Chlorophenyl-5-ethylthiomethylthiophen-2-yl = ketone = N-cyclopentylcarbonylhydrazone (Compound No. 1-306), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-cyclohexylcarbonyl Hydrazone (Compound No. 1-30
7), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-allyloxycarbonylhydrazone (Compound No. 1-314), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl =
Ketone = N-methoxyacetylhydrazone (Compound No. 1-319), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-phenoxyacetylhydrazone (Compound No. 1-321), 4-chlorophenyl = 5 -Ethylthiomethylthiophen-2-yl = ketone = N- (4-chlorobenzoyl) hydrazone (Compound No. 1-334), 4-chlorophenyl = 5-
Ethylthiomethylthiophen-2-yl = ketone = N-
(Pyridinecarbo-2-yl) hydrazone (compound number 1-336), 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (compound number 1-344), 4-chlorophenyl = 5-ethylsulfinylmethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-345), 4-chlorophenyl = 5
-Ethylthiomethylthiophen-2-yl = ketone = N
-Ethoxycarbonylhydrazone (Compound No. 1-34)
6), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-propoxycarbonylhydrazone (Compound No. 1-348), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-isobutoxycarbonylhydrazone (Compound No. 1-351), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-allyloxycarbonylhydrazone (Compound No. 1-353),
4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N- (2-methoxyethoxycarbonyl) hydrazone (Compound No. 1-354), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-
Il = ketone = N- (2-chloroethoxycarbonyl)
Hydrazone (Compound No. 1-356), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-methylaminocarbonylhydrazone (Compound No. 1-376), 4-chlorophenyl = 5-ethylthiomethylthiophene -2-yl = ketone = N-ethoxymethyl-N-methoxycarbonylhydrazone (Compound No. 1-400), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-methoxycarbonyl-N-methylthio Methylhydrazone (Compound No. 1-401), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-ethoxycarbonylmethyl-N-methoxycarbonylhydrazone (Compound No. 1-403), 4-chlorophenyl = 5-
Ethylthiomethylthiophen-2-yl = ketone = N-
Cyanomethyl-N-methoxycarbonylhydrazone (Compound No. 1-404), 4-chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-methoxycarbonyl-N-propionylhydrazone (Compound No. 1-409), 4 -Chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = hydrazone (Compound No. 1-437), 4-chlorophenyl =
5-ethylsulfonylmethylthiophen-2-yl = ketone = N-acetylhydrazone (Compound No. 1-43
8), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-propionylhydrazone (compound No. 1-439), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N -Butyrylhydrazone (compound number 1-4)
40), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-cyclopropylcarbonylhydrazone (Compound No. 1-452), 4
-Chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-cyclohexylcarbonylhydrazone (Compound No. 1-455), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-
Il = ketone = N-cinnamoylhydrazone (compound No. 1-457), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-methoxyacetylhydrazone (compound No. 1-466), 4
-Chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-phenoxyacetylhydrazone (Compound No. 1-468), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl =
Ketone = N- (2-methylthiopropionyl) hydrazone (Compound No. 1-479), 4-chlorophenyl = 5
-Ethylsulfonylmethylthiophen-2-yl = ketone = N- (4-chlorobenzoyl) hydrazone (Compound No. 1-481), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-
(Thiophenecarb-2-yl) hydrazone (Compound No. 1-486), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-491),
4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-propoxycarbonylhydrazone (Compound No. 1-493), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-butoxy Carbonylhydrazone (Compound No. 1-495), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-
Isobutoxycarbonylhydrazone (Compound No. 1-4
96), 4-chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-allyloxycarbonylhydrazone (Compound No. 1-498), 4-
Chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N- (2-methoxyethoxycarbonyl) hydrazone (Compound Nos. 1-499), 4-
Chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N- (2-chloroethoxycarbonyl) hydrazone (Compound No. 1-501), 4-chlorophenyl = 5-trifluoromethylthiomethylthiophen-2-yl = ketone = Hydrazone (compound number 1
-579), 4-chlorophenyl = 5-trifluoromethylthiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-58)
2), 4-chlorophenyl = 5- (2,2,2-trifluoroethyl) thiomethylthiophen-2-yl = ketone = hydrazone (Compound No. 1-584), 4-chlorophenyl = 5- (2,2, 2-trifluoromethyl) thiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-587), 4-
Chlorophenyl = 5-propylthiomethylthiophene-
2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-597), 4-chlorophenyl = 5-
Isopropylthiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-
602), 4-chlorophenyl = 5-tert-butylthiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-612), 4
-Chlorophenyl = 4-chloro-5-ethylthiomethylthiophen-2-yl = ketone = N-methoxycarbonylhydrazone (Compound No. 1-622), 4-chlorophenyl = 4-bromo-5-ethylthiomethylthiophen-2- Il = ketone = N-methoxycarbonylhydrazone (Compound No. 1-632) and 4-chlorophenyl =
5-allylthiomethylthiophen-2-yl = ketone =
N-methoxycarbonylhydrazone (Compound No. 1-6
53).

[0084]

BEST MODE FOR CARRYING OUT THE INVENTION The heteroarylhydrazone compound of the present invention can be produced by the methods of Steps A to I described below.

Step A

[0086]

Embedded image In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, m, Y,
n and p are as defined above.

In the step A, the carbonyl compound represented by the general formula (IV) is reacted with the hydrazine compound represented by the general formula (V) or a hydrate or salt thereof to produce the compound represented by the general formula (I) of the present invention. This is a step of producing the heteroarylhydrazone compound represented by the formula (1).

The amount of compound (V) or a hydrate thereof used in this step is usually in the range of 1 mole of compound (IV)
1.0 to 20.0 mol, preferably 1.0 to 1
0.0 mol.

This step can be performed in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether, Ethers such as dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide and N Amides such as methyl-2-pyrrolidone; sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons such as cyclohexane and heptane; pyridine and pyridines such as picoline; fatty acids such as acetic acid;
Water; and a mixed solvent thereof, preferably alcohols or ethers, and more preferably methanol or ethanol.

The amount of the solvent used depends on the amount of the compound (IV)
The amount is usually 0.1 to 20.0 L, preferably 1 to 10.0 L, per mol.

This step can be carried out in the presence or absence of an acid.

The acid used is not particularly limited as long as it has an ordinary pH of 6 or less. For example, mineral acids such as hydrochloric acid, sulfuric acid, perchloric acid and nitric acid; formic acid, acetic acid and propionic acid; Carboxylic acids; sulfonic acids such as methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid monohydrate; acid addition salts of amines such as pyridine hydrochloride and triethylamine hydrochloride; aluminum chloride, tetrachloride Titanium, metal halides such as zinc chloride and Lewis acids such as boron trifluoride etherate are preferred, and carboxylic acids or sulfonic acids are preferred.

The amount of the acid used is usually the same as that of the compound (I
V) 0.01 to 100.0 mol per 1 mol,
Preferably, it is 0.01 to 30.0 mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -10 ° C to the reflux temperature in the reaction system, and preferably from room temperature to 150 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents and the like, but is usually 0.5 to 48 hours.
Preferably, it is 1 to 24 hours.

Step B

[0098]

Embedded imageIn the above formula, R¹, R^Two, R^Three, R^Four, R^Five, A, X, m, Y,
n and p are as defined above, and R^7bIs a halogen source
Child, C₁~ C₆Alkylsulfonyloxy group or C ₆~ C
_TenArylsulfonyloxy group (the arylsulfonyl group
A luoxy group is the same or different 1 to 5 halo
Gen atom or C₁~ C₆Substituted by an alkyl group
Good. ) And Z represents the formula -S (O)_qM (where q
Represents 0 or 2, and M represents an alkali metal. )so
Shows the group represented.

In step B, the compound (I) of the present invention is produced by reacting the heteroarylhydrazone compound represented by the general formula (IIIb) with the alkali metal salt (VIa) represented by the general formula (VI) This is the step of performing

The amount of compound (VI) used in this step is usually 1.0 to 1.0 mol per mol of compound (IIIb).
It is 10.0 moles, and preferably 1.0 to 3.0 moles.

This step can be performed in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether, Ethers such as dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide and N Amides such as methyl-2-pyrrolidone; sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons such as cyclohexane and heptane; pyridine and pyridines such as picoline; fatty acids such as acetic acid;
Water; and a mixed solvent thereof, preferably amides, sulfoxides, ethers or alcohols, more preferably methanol, ethanol or N,
N-dimethylformamide.

The amount of the solvent used is usually the same as that of the compound (I
IIb) It is 0.05 to 100.0 L, preferably 0.1 to 10.0 L, per 1 mol.

Compound (VI) in this step is represented by the formula R ¹
A compound represented by S (O) _q H (wherein R ¹ and q have the same meanings as described above), an alkali metal, a hydride of an alkali metal, a hydroxide of an alkali metal, and an alkali of a lower alcohol. It can be prepared by reacting with a metal salt, an alkali metal carbonate or an organic amine.
Formula R ¹ S (O) _q X ¹ } wherein R ¹ and q have the same meanings as described above, and X ¹ represents a halogen atom (preferably a chlorine atom or a bromine atom). A compound represented by｝,
It can also be prepared by reacting with an alkali metal sulfite.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -10 ° C to the reflux temperature in the reaction system, and preferably from room temperature to 150 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents and the like, but is usually 3 minutes to 24 hours, preferably 0.1 to 24 hours.

Step C

[0108]

Embedded image In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, m, Y,
n and p are as defined above, R ^7c is a mercapto group, a C ₂ -C ₇ alkylcarbonylthio group or an amidinosulfenyl group, Z ^b is a halogen atom, C ₁ -C ₆
An alkylsulfonyloxy group or a C _{6 to} C ₁₀ arylsulfonyloxy group (the arylsulfonyloxy group may be substituted by the same or different 1 to 5 halogen atoms or C _{1 to} C ₆ alkyl groups); Show.

In step C, the compound of the present invention (I) is produced by reacting the heteroarylhydrazone compound of the formula (IIIb) with the compound of the formula (VI) in the presence of a base. It is a process.

The amount of compound (VI) used in this step is usually 1.0 to 1.0 mol per mol of compound (IIIb).
It is 10.0 moles, and preferably 1.0 to 5.0 moles.

The base to be used is not particularly limited as long as it usually has a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; Hydroxides of alkaline earth metals such as; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; Metal hydrides; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; and triethylamine, N, N-
Examples include organic bases such as dimethylaniline and pyridine, preferably hydroxides of alkali metals or carbonates of alkali metals, and more preferably sodium hydroxide, potassium hydroxide or sodium carbonate. .

The amount of the base to be used depends on the amount of the compound (III)
b) It is usually 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol.

This step can be performed in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether; Ethers such as dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide and N Amides such as methyl-2-pyrrolidone; sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons such as cyclohexane and heptane; pyridine and pyridines such as picoline; fatty acids such as acetic acid;
Water; and a mixed solvent thereof. Preferred are alcohols, ethers, amides and water, and more preferred are methanol, ethanol, tetrahydrofuran and N, N-dimethylformamide.

The amount of the solvent used depends on the amount of the compound (III)
b) It is usually 0.1 to 20.0 L per 1 mol,
Preferably, it is 1.0 to 10.0 L.

The reaction temperature varies depending on the starting compounds, reaction reagents, solvents and the like, but is usually from -40 ° C to the reflux temperature in the reaction system, preferably from 0 to 150 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents, etc., but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

Step D

[0119]

Embedded image In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, m, Y,
n and p have the same meaning as described above, and R ^7b represents a hydroxyl group. ).

In the step D, the heteroarylhydrazone compound represented by the general formula (IIIb) is reacted with diaminochlorophosphine in the presence of a solvent and a base, and then the disulfide represented by the general formula (VI) is reacted. Let me
This is a step of producing the compound (I) of the present invention.

The amount of diaminochlorophosphine used in this step is usually
1.0 to 6.0 mol, preferably 1.0 to 3.0 mol.
Is a mole.

The base to be used is not particularly limited as long as it usually shows a pH of 8 or more. Examples thereof include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; and hydroxides of calcium hydroxide and magnesium hydroxide. Hydroxides of alkaline earth metals such as; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; Metal hydrides; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; and triethylamine, N, N-
Organic bases such as dimethylaniline and pyridine are preferred, preferably organic bases, more preferably
Triethylamine or pyridine.

The amount of the base to be used depends on the amount of the compound (III)
b) relative to 1 mol, usually 1.0 to 6.0 mol;
Preferably, it is 1.0 to 3.0 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane, benzene, toluene. Aromatic hydrocarbons such as benzene, xylene and chlorobenzene; nitriles such as acetonitrile; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; dimethyl sulfoxide and Sulfoxides such as sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; Yo Such pyridines; and the like a mixture of these solvents, preferably an ether or an ester, and more preferably tetrahydrofuran or ethyl acetate.

The amount of the solvent used depends on the amount of the compound (III)
b) It is usually 0.1 to 10.0 L per 1 mol,
Preferably, it is 1.0 to 5.0 L.

The amount of compound (VI) to be used is generally 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol of compound (IIIb).

The reaction temperature of the reaction for adding diaminochlorophosphine varies depending on the starting compound, base, solvent and the like, but is usually from -40 ° C to the reflux temperature in the reaction system.
Preferably, it is 0 to 100 ° C.

The reaction time for the reaction of adding diaminochlorophosphine varies depending on the reaction temperature, the starting compounds, the reaction reagents and the like, but is usually from 3 minutes to 48 hours, and preferably from 3 minutes to 48 hours.
0.1 to 24 hours.

The reaction temperature of the reaction for adding disulfides varies depending on the starting compound, base, solvent and the like.
−40 ° C. to the reflux temperature in the reaction system, preferably
0-100 ° C.

The reaction time of the reaction for adding the disulfides varies depending on the reaction temperature, the starting compounds, the reaction reagents and the like, but is usually 3 minutes to 48 hours, and preferably 0.1 minute to 48 hours.
~ 24 hours.

Step E

[0132]

Embedded imageIn the above formula, R¹, R^Two, R^Three, A, X, m, Y, n and p are
Is as defined above,^4aIs a hydrogen atom, C₁~ C₆Al
A kill group (the alkyl group may be the same or different
5 halogen atoms or 1 C₁~ C₆Alkoxy
Group, C₁~ C₆Alkylthio group, C_Two~ C₇Alkoxycal
Bonyl group, pyridyloxy group, cyano group or hydroxyl group
May be substituted by ), C_Two~ C₆Alkenyl group
(The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C_Two
~ C₆Alkynyl group, formyl group, C_Two~ C_TenAlkylka
Rubonyl group ｛the alkylcarbonyl group is the same or different
Are different from 1 to 5 halogen atoms or 1 C₁~
C₆Alkoxy group, phenoxy group (the phenoxy group
Are the same or different 1 to 5 C₁~ C₆Archi
Group, C₁~ C₆Placed by alkoxy group or halogen atom
May be replaced. ), C₁~ C₆Alkylthio group,
A nilthio group (the phenylthio group may be the same or different
Only one to five C ₁~ C₆Alkyl group, C₁~ C₆Arco
Substituted by a xy group or a halogen atom
No. ), Carboxyl group, C_Two~ C₇Alkoxycarboni
And it may be substituted by a methyl group or a cyano group. ｝,
C_Three~ C₇Alkenylcarbonyl group (the alkenylcal
The carbonyl group is the same or different 1 to 5 halogeno groups.
Atom or one phenyl group or C_Two~ C₇Alkoki
It may be substituted by a cyclocarbonyl group. ), C_Three~
C₇Alkynylcarbonyl group, benzoyl group
The zoyl group is the same or different 1 to 5 halogeno groups.
Atom or C₁~ C₆Alkyl group or one carboxy
Sil group or C_Two~ C₇By an alkoxycarbonyl group
It may be substituted. ), Pyridylcarbonyl group (
The pyridylcarbonyl group may be the same or different from 1 to
4 halogen atoms or C₁~ C₆Substituted by alkyl group
May have been. ), Thienylcarbonyl group (the thienyl
1 to 3 identical or different carbonyl groups
A halogen atom or C₁~ C₆Substituted by an alkyl group
May be. ), C_Two~ C₇Alkyl (thiocarbonyl)
Group {-C (= S)-}, phenyl (thiocarbonyl) group
｛-C (= S)-｝, C_Two~ C₇Alkoxycarbonyl group
(The alkoxycarbonyl groups may be the same or different
1 to 5 halogen atoms or 1 C₁~ C₆Arco
Xy group, C₁~ C₆By alkylthio or cyano group
May be substituted. ), C_Three~ C₇Alkenyloxy
Carbonyl group, phenoxycarbonyl group (the phenoxy
Cicarbonyl groups are the same or different and 1 to 5
Halogen atom or C₁~ C₆Substituted by an alkyl group
May be. ), C_Two~ C₇(Alkylthio) carbonyl group
{-SC (= O)-}, (phenylthio) carbonyl
Group, C_Two~ C₇Alkyldithiocarbonyl group, phenyldi
Thiocarbonyl group, C_Three~ C₈Alkylcarbonylcarbo
Nyl group, phenylcarbonylcarbonyl group, C_Three~ C₈A
Lucoxycarbonylcarbonyl group, phenoxycarbonyl
Carbonyl group, aminocarbonyl group
A bonyl group may be one or two identical or different C₁~
C₆Alkyl group, C_Two~ C₇An alkoxycarbonyl group,
(C_Two~ C₇Alkoxycarbonyl) C₁~ C₆Alkyl group
Or one phenyl group (the phenyl group may be the same or different
Is substituted by 1 to 5 different halogen atoms
May be. ) May be substituted.ア ミ ノ, aminoti
Ocarbonyl group (the aminothiocarbonyl group is the same
Or one or two different C₁~ C₆By alkyl group
May be substituted. ), Furanylcarbonyl group (this
The furanylcarbonyl groups may be the same or different.
It may be substituted by up to three halogen atoms. ),
Pyrazolylcarbonyl group (the pyrazolylcarbonyl group
Are the same or different one or two C₁~ C₆Archi
Or a halogen atom. ),
C₁~ C₆Alkylsulfonyl group, phenylsulfonyl group
(The phenylsulfonyl groups may be the same or different
1 to 5 C₁~ C₆Alkyl group, C₁~ C₆Alkoxy
It may be substituted by a group or a halogen atom. ) Or
An aminosulfonyl group (the aminosulfonyl group is the same
Or one or two different C₁~ C₆By alkyl group
May be substituted. ) And R^5aIs C_Two~ C_Ten
Alkylcarbonyl group ｛the alkylcarbonyl group is
1 to 5 identical or different halogen atoms or 1
C₁~ C₆Alkoxy group, phenoxy group (the pheno group
The xy group is the same or different from one to five C₁~ C₆
Alkyl group, C₁~ C₆To an alkoxy group or a halogen atom
It may be more substituted. ), C₁~ C₆Alkylthio
Group, phenylthio group (the phenylthio group
Or 1 to 5 different C₁~ C₆Alkyl group, C₁~
C₆Substituted by an alkoxy group or a halogen atom
May be. ), Carboxyl group, C_Two~ C₇Alkoxycal
May be substituted by a bonyl group or a cyano group
No. ｝, C_Three~ C₇Alkenylcarbonyl group (the
1 to 5 identical or different carbonyl groups
A halogen atom or one phenyl group or C_Two~ C₇
May be substituted by an alkoxycarbonyl group
No. ), C_Three~ C₇Alkynylcarbonyl group, benzoyl
Groups (the benzoyl groups may be the same or different
5 halogen atoms or C₁~ C₆Alkyl group or 1
Carboxyl groups or C _Two~ C₇Alkoxycarbo
It may be substituted by a nyl group. ), Pyridylcarbo
Nyl group (the pyridylcarbonyl group may be the same or different
1 to 4 halogen atoms or C₁~ C₆Alkyl
May be substituted by a group. ), Thienylcarbonyl
Groups (the thienylcarbonyl groups are the same or different
1 to 3 halogen atoms or C₁~ C₆To the alkyl group
It may be more substituted. ), C_Two~ C₇Alkyl (thio
Carbonyl) group {-C (= S)-}, phenyl (thioca
Rubonyl) group {-C (= S)-}, C_Two~ C₇Alkoxy
A carbonyl group (the same alkoxycarbonyl group
Or different 1 to 5 halogen atoms or 1 C
₁~ C₆Alkoxy group, C₁~ C₆Alkylthio group or
It may be substituted by a cyano group. ), C_Three~ C₇Al
Kenyloxycarbonyl group, phenoxycarbonyl group
(The phenoxycarbonyl groups may be the same or different.
1 to 5 halogen atoms or C₁~ C₆To the alkyl group
It may be more substituted. ), C_Two~ C₇(Alkyl
E) carbonyl group {-SC (= O)-}, (phenyl
Thio) carbonyl group, C_Two~ C₇Alkyl dithiocarboni
Group, phenyldithiocarbonyl group, C_Three~ C₈Alkyl
Carbonylcarbonyl group, phenylcarbonylcarboni
Group, C_Three~ C₈Alkoxycarbonylcarbonyl group,
Phenoxycarbonylcarbonyl group, aminocarbonyl group
{The aminocarbonyl groups are the same or different.
Or two C₁~ C₆Alkyl group, C_Two~ C₇Alkoxyka
Rubonyl group, (C_Two~ C₇Alkoxycarbonyl) C₁~
C₆An alkyl group or one phenyl group (the phenyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. )
No. ｝, Aminothiocarbonyl group (the aminothiocar
A bonyl group may be one or two identical or different C₁~
C₆It may be substituted by an alkyl group. ), Fulani
Carbonyl group (the furanylcarbonyl group is the same
Or 1 to 3 different halogen atoms
You may be. ), Pyrazolylcarbonyl group (
The zolylcarbonyl group may be the same or different 1 or 2
C₁~ C₆Substituted by an alkyl group or a halogen atom
You may be. ), C₁~ C₆Alkylsulfonyl group,
Phenylsulfonyl group (the phenylsulfonyl group is
1 to 5 different Cs₁~ C₆Alkyl group,
C₁~ C₆Substituted by an alkoxy group or a halogen atom
May be. ) Or aminosulfonyl group (the aminos
The rufonyl group may be the same or different and one or two C₁
~ C₆It may be substituted by an alkyl group. )
And E is a halogen atom, a hydroxyl group or a formula -OR^5a(formula
Medium, R^5aHas the same significance as described above. Represents a group represented by)
You.

In the step E, a heteroarylhydrazone compound represented by the general formula (VII) is added to the compound represented by the general formula (VIII)
Is a step of producing the compound (Ia) of the present invention by reacting the compound represented by the formula (I) When E in the general formula (VIII) is a hydroxyl group, the compound (VIII) is reacted with the compound (VIII) in the presence of a solvent, a base and a condensing agent, whereby the compound of the present invention (Ia) is obtained. Can be manufactured.

The amount of compound (VIII) to be used in this step is usually 1.0 to 1.0 mol per 1 mol of compound (VII).
It is 10.0 moles, and preferably 1.0 to 5.0 moles.

The base to be used is not particularly limited as long as it generally has a pH of 8 or more. Examples thereof include alkali metal carbonates such as sodium carbonate and potassium carbonate; and alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate. Metal bicarbonates; and triethylamine;
Examples include organic bases such as N, N-dimethylaniline and pyridine, preferably organic bases, more preferably triethylamine or pyridine.

The amount of the base used is determined according to the amount of compound (VII)
Usually, it is 1.0 to 20.0 mol, preferably 1.0 to 10.0 mol, per 1 mol.

The condensing agent to be used is not particularly limited as long as it is a reagent having a condensing ability. For example, C ₁ -C ₄ alkyl chloroformate such as methyl chloroformate and ethyl chloroformate; dichloro-1 iodide Pyridinium salts such as -methylpyridinium; and carbodiimides such as dicyclohexylcarbodiimide, preferably pyridinium salts, and more preferably 2 iodide.
Chloro-1-methylpyridinium.

The amount of the condensing agent to be used depends on the amount of the compound (VI
I) Usually, 1.0 to 6.0 mol per 1 mol,
Preferably, it is 1.0 to 3.0 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as toluene, xylene and chlorobenzene; nitriles such as acetonitrile; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; dimethyl sulfoxide And halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridine and picoline No Pyridines; and a mixed solvent thereof, preferably ethers, halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, Methylene chloride, ethyl acetate or toluene.

The amount of the solvent used is determined according to the amount of the compound (VII)
It is usually 0.05 to 20.0 L, preferably 0.1 to 10.0 L, per 1 mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -40 ° C to the reflux temperature in the reaction system, preferably from 0 to 100 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents, etc., but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours. (Ii) When E in the general formula (VIII) is a halogen atom or a group represented by the formula —OR ^5a , wherein R ^5a has the same meaning as described above, the compound (VII) ,
The compound (Ia) of the present invention can be produced by reacting the compound (VIII) in the presence of a solvent and a base.

The amount of compound (VIII) to be used in this step is generally 1.0 to 1.0 mol per mol of compound (VII).
It is 20.0 mol, preferably 1.0 to 10.0 mol.

The base to be used is not particularly limited as long as it generally has a pH of 8 or more. Examples thereof include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; and salts such as sodium carbonate and potassium carbonate. Alkali metal carbonates; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkali metal hydrides such as sodium hydride and potassium hydride; alkoxides such as sodium methoxide and sodium ethoxide And triethylamine, N, N-
Examples include organic bases such as dimethylaniline and pyridine, preferably alkali metal hydrides, alkoxides or organic bases, more preferably sodium hydride or sodium methoxide.

The amount of the base used is determined according to the amount of the compound (VII)
Usually, it is 1.0 to 20.0 mol, preferably 1.0 to 10.0 mol, per 1 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; benzene, Aromatic hydrocarbons such as toluene, xylene and chlorobenzene; nitriles such as acetonitrile; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; dimethyl sulfoxide And halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridine and picoline No Such pyridines; and the like mixed solvents thereof, preferably, ethers, esters, aliphatic hydrocarbons, and amides or aromatic hydrocarbons, more preferably tetrahydrofuran or N, N
-Dimethylformamide.

The amount of the solvent used is determined according to the amount of the compound (VII)
It is generally 0.1 to 20.0 L, preferably 1.0 to 10.0 L, per 1 mol.

The reaction temperature varies depending on the starting compound, the reaction reagent, the solvent and the like, but is usually from -40 ° C to the reflux temperature in the reaction system, preferably from 0 to 100 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents and the like, but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

Step F

[0151]

Embedded image In the formula, R ¹ , R ² , R ³ , A, X, m, Y, n and p have the same meanings as described above, and R ⁸ and R ⁹ are the same or different and represent a hydrogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, C ₂ -C ₇ alkoxycarbonyl group, phenoxycarbonyl group or amino group (the amino group is the same or different one or two C ₁
It may be substituted by -C ₆ alkyl group. ), Provided that R ⁸ and R ⁹ are not simultaneously hydrogen atoms.

In step F, compound (IX) and compound (X) are used in the presence or absence of a solvent, in the presence or absence of an acid.
Can be carried out according to step A.

Step G

[0154]

Embedded image In the above formula, R ¹ , R ² , R ³ , R ⁸ , R ⁹ , A, X, m, Y,
n and p have the same meaning as described above, and R ^4b is a C ₂ -C ₁₀ alkylcarbonyl group. The alkylcarbonyl group is the same or different from 1 to 5 halogen atoms or 1 C ₁ -C ₆ An alkoxy group, a phenoxy group (the phenoxy group may be substituted by the same or different 1 to 5 C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms), C _1- A C ₆ alkylthio group,
A phenylthio group (the phenylthio group may be substituted by the same or different 1 to 5 C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms) or a cyano group; May be. ｝, A C ₃ -C ₇ alkenylcarbonyl group (the alkenyl carbonyl group may be substituted by the same or different 1 to 5 halogen atoms or one phenyl group), C ₃ -C ₇ alkynylcarbonyl A benzoyl group (the benzoyl group may be substituted with the same or different 1 to 5 halogen atoms or a C _{1 to} C ₆ alkyl group), a pyridylcarbonyl group (the pyridylcarbonyl group is the same or different the different 1 to 4 halogen atoms or C ₁ -C ₆ alkyl group may be substituted.), thienyl group (the thienylcarbonyl group being the same or different 1 to 3
May be substituted by _one halogen atom or a C ₁ -C ₆ alkyl group. ), C ₂ -C ₇ alkyl (thiocarbonyl) group {-C (= S) -} , phenyl (thiocarbonyl) group {-C (= S) -} , C 2 ~C 7 alkoxycarbonyl group (the alkoxy The carbonyl group is the same or different from one to five halogen atoms or one C ₁ -C ₆
It may be substituted by an alkoxy group, a C ₁ -C ₆ alkylthio group or a cyano group. ), C ₃ -C ₇ alkenyloxycarbonyl group, a phenoxycarbonyl group (said phenoxycarbonyl group may be substituted by same or different 1 to 5 halogen atoms or C ₁ -C ₆ alkyl group.), C ₂ -C ₇ (alkylthio) carbonyl group {-S-C (= O) -}, ( phenylthio) carbonyl group, C ₂ -C ₇ alkyl dithio group, a phenyl dithio group, C ₃ -C ₈ alkylcarbonyl Carbonyl group, phenylcarbonylcarbonyl group, C ₃
-C ₈ alkoxycarbonyl group, a phenoxycarbonyl group, an amino group {said aminocarbonyl group being the same or different 1 or 2 C ₁ -C ₆ alkyl group or one phenyl group (said phenyl group May be substituted with 1 to 5 identical or different halogen atoms.). ｝, An aminothiocarbonyl group (the aminothiocarbonyl group is the same or different one or two C
It may be substituted by ₁ -C ₆ alkyl group. ), C ₁
-C ₆ alkylsulfonyl group, phenylsulfonyl group (the phenylsulfonyl group may be substituted by _{1 to} 5 identical or different C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. .) Or an aminosulfonyl group (the aminosulfonyl group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups).

In the step G, the heteroarylhydrazone compound represented by the general formula (VIIb) (compound (VII), wherein R ⁴ is a group containing a carbonyl group) is halogenated, and compound (Ic) is converted to a compound (Ic). In this step, the compound (Ic) is reacted with the compound represented by the general formula (XII) to produce the compound (Ib) of the present invention. (I) Step G-1 is a step of halogenating compound (VIIb) with a halogenating agent to produce compound (Ic).

The halogenating agent used in this step is not particularly limited as long as it can halogenate ordinary organic compounds. Examples thereof include phosphorus trichloride, phosphorus pentachloride, thionyl chloride and triphenylphosphine-tetrachloride. Chlorinating agents such as a mixture of carbon; iodination agents such as iodine; and brominating agents such as a mixture of triphenylphosphine-bromine, preferably a mixture of triphenylphosphine-carbon tetrachloride. It is.

The amount of the halogenating agent to be used is generally 1.0 to 20.0 mol per 1 mol of compound (VIIb).
Mol, preferably 1.0 to 10.0 mol.

This step is performed in the presence or absence of a solvent.

The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but is preferably an ether such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane. Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; such as acetonitrile, propionitrile Nitriles; hexane,
Aliphatic hydrocarbons such as cyclohexane and heptane; pyridines such as pyridine and picoline; and a mixed solvent thereof, and are preferably ethers, nitriles or esters, more preferably Tetrahydrofuran, acetonitrile or ethyl acetate.
Further, the halogenating agent can also be used as a solvent.

The amount of the solvent used depends on the amount of the compound (VII)
b) It is usually 0.1 to 20.0 L, preferably 1.0 to 10.0 L, per 1 mol.

The reaction temperature depends on the starting compound, halogenating agent,
Although it depends on the solvent and the like, it is usually from 0 ° C to the reflux temperature in the reaction system, and preferably from 0 to 100 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents and the like, but is usually from 3 minutes to 48 hours, preferably from 0.1 to 24 hours. (Ii) In the step G-2, the compound (Ic) is converted to a compound (X
This is a step of producing compound (Ib) by reacting with compound II).

The amount of compound (XII) used in this step is usually 1.0 to 1 based on 1 mol of compound (Ic).
The amount is 0.0 mol mol, preferably 1.0 to 5.0 mol.

This step can be performed in the presence or absence of a base.

The base to be used is not particularly limited as long as it usually has a pH of 8 or more. For example, alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate Metal bicarbonates and the like; and triethylamine,
Examples include organic bases such as N, N-dimethylaniline and pyridine, preferably organic bases, more preferably triethylamine or pyridine.

This step is performed in the presence or absence of a solvent.

The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Preferably, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane are used. Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; such as acetonitrile, propionitrile Nitriles; hexane,
Aliphatic hydrocarbons such as cyclohexane and heptane; pyridines such as pyridine and picoline; and a mixed solvent thereof, and are preferably ethers, nitriles or esters, more preferably Tetrahydrofuran, acetonitrile or ethyl acetate.

The amount of the solvent used depends on the amount of the compound (Ic)
It is usually 0.1 to 20.0 L, preferably 1.0 to 10.0 L, per mole.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from 0 ° C. to the reflux temperature in the reaction system, and preferably from 0 ° C. to 100 ° C.

The reaction time varies depending on the reaction temperature, raw material compounds, reaction reagents and the like, but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

Step H

[0172]

Embedded image In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, m, Y and p are as defined above, and s is 1 or 2.

In the step H, the heteroarylhydrazone compound represented by the general formula (XI) is oxidized using an oxidizing agent, and the compound of the present invention (Ie) ｛n is selected from n in the general formula (I).
Is 1 or 2. This is the step of manufacturing｝.

The oxidizing agent used in this step is not particularly limited as long as it is an ordinary oxidizing agent for a sulfur atom.
For example, peroxides such as hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate and oxone (potassium hydrogen peroxosulfate, registered trademark of EI DuPont); N-chlorosuccinimide Halogenating agents; hypochlorites such as sodium hypochlorite;
And oxygen, preferably a peroxide, more preferably hydrogen peroxide or m-chloroperbenzoic acid.

The amount of the oxidizing agent to be used, when s is 1, is usually from 1.0 to 3 to 1 mol of compound (XI).
0 mol, preferably 1.05 to 2.2 mol, and when s is 2, with respect to 1 mol of the compound (XI)
Usually, it is 2.0 to 10.0 mol, preferably 2.0 mol
5 to 5.0 moles.

When hydrogen peroxide is used as the oxidizing agent,
This step can be oxidized in the presence of a catalyst.

Examples of the catalyst used include sodium tungstate.

The amount of the catalyst used is usually 0.001 to 0.9 mol per 1 mol.

This step can be performed in the presence or absence of a solvent.

The solvent to be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether, dimethoxy Ethers such as ethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone Amides; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; such as hexane, cyclohexane and heptane. Aliphatic hydrocarbons; pyridines such as pyridine and picoline; ketones such as acetone, methyl ethyl ketone and cyclohexanone; fatty acid carboxylic acids such as acetic acid; water; and mixed solvents thereof, preferably ether. , Halogenated hydrocarbons or esters, more preferably tetrahydrofuran, methylene chloride, dichloroethane or ethyl acetate.

The amount of the solvent used is the same as that of compound (XI)
It is usually 0.1 to 20.0 L, preferably 1.0 to 10.0 L, per mole.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -20 ° C to the reflux temperature in the reaction system, preferably from 10 to 100 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents and the like, but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

Step I

[0185]

Embedded image In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, m, Y,
n and p are as defined above, and GH is, for example, hydrogen halide such as hydrogen chloride or hydrogen bromide; other inorganic acids such as sulfuric acid, nitric acid, phosphoric acid; methanesulfonic acid, p -Organic sulfonic acids such as toluenesulfonic acid; or other organic acids such as trifluoroacetic acid, oxalic acid, preferably hydrogen halide or organic sulfonic acids, more preferably hydrogen chloride or Methanesulfonic acid.

In Step I, the compound (I) is converted to a compound represented by the general formula (XI)
This is a step of reacting an acid represented by II) to produce a salt of the present invention represented by the general formula (Id).

The amount of the acid (XIII) used in this step is usually from 1.0 to 10.3 based on 1 mol of the compound (I).
0 mol, preferably 1.0 to 5.0 mol.

This step can be carried out in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether, dimethoxy Ethers such as ethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline;
Fatty acid carboxylic acids such as acetic acid; water; and a mixed solvent thereof, preferably alcohols, ethers or halogenated hydrocarbons, more preferably tetrahydrofuran or methylene chloride.

The amount of the solvent to be used is generally 0.1 to 20.0 L, preferably 1.0 to 10.0 L, per 1 mol of compound (I).

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -30 ° C to the reflux temperature in the reaction system, preferably from 0 to 40 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents and the like, but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

The novel synthetic intermediates represented by the general formulas (II) and (III) can be produced, for example, by the methods of Steps J to O shown below.

The reaction formulas of Steps J to N are shown below.

[0195]

Embedded image [Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, m, Y,
n and p are as defined above, and W ¹ and W ² are each independently a halogen atom, a C ₁ -C ₆ alkylsulfonyloxy group or a benzenesulfonyloxy group (the benzenesulfonyloxy group is the same or May be substituted by _{1 to} 5 different C ₁ -C ₆ alkyl groups or halogen atoms), and R ¹⁰ is hydrogen, C ₁ -C ₆
It represents an alkylcarbonylthio group or an amidinosulfenyl group, M ¹ represents an alkali metal, M ² represents an alkali metal or ammonium ion, and r represents 1 or 2. Step J In step J, a halogenocarbonyl compound represented by the general formula (XIV) is reacted with a sulfinic acid salt represented by the general formula (XV) to form a sulfonylcarbonyl compound represented by the general formula (IVa)に お い て In the compound (IV), n is 2
A compound that is This is the step of manufacturing｝.

The sulfinate used in this step (X
The amount of V) is usually in the range of 1 mole of compound (XIV).
1.0 to 5.0 mol, preferably 1.0 to 3.0 mol.
It is.

This step can be carried out in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether, dimethoxy alcohol and the like. Ethers such as ethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone Amides; sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; acetone, methyl ethyl ketone and Ketones such as cyclohexanone; water; fatty acids such as acetic acid and mixed solvents thereof and the like, preferably, an amide, a ketone, ethers or esters, more preferably,
N, N-dimethylformamide, acetone, tetrahydrofuran or ethyl acetate.

The amount of the solvent used is determined according to the amount of the compound (XIV)
It is generally 0.1 to 20.0 L, preferably 1.0 to 10.0 L, per 1 mol.

The reaction temperature varies depending on the starting compound, the solvent and the like, but is usually from 0 ° C. to the reflux temperature in the reaction system.
Preferably, it is 10 to 100 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents, etc., but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

The sulfinate used in this step (X
V) is a commercially available product or a known method {for example, a journal
J. Che, The Chemical Society, p. 636, 1945
m. Soc., 636 (1945) or Journal of the American Chemical Society, 1974, Vol. 96, 2275.
Page J. Am. Chem. Soc., 96, 2275 (1974). ｝ Can be obtained.

Step K Step K is a step of reacting compound (XIV) with a compound represented by formula (XVI) to produce a thiocarbonyl compound represented by formula (IVb).

This step can be performed according to step J.

Step L In step L, compound (XIX) is reacted with a compound represented by general formula (XVII), and carbonyl compound represented by general formula (IVc)） compound (IV) wherein n is A compound which is 0. This is the step of manufacturing｝.

The amount of the compound (XVII) used in this step is 1.0 to 5.0 based on 1 mol of the compound (XIX).
Mole, and preferably 1.0 to 3.0 mole.

This step can be performed in the presence or absence of a base.

The base to be used is not particularly limited as long as it usually has a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; and bases such as sodium carbonate and potassium carbonate Alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; and organic bases such as triethylamine, N, N-dimethylaniline and pyridine. Hydroxides or carbonates or organic bases of
More preferably, it is sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.

The amount of the base to be used is determined based on the amount of the compound (XIX)
It is usually 0.1 to 20 mol, preferably 0.1 to 10.0 mol, per 1 mol.

This step can be performed in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include alcohols such as methanol and ethanol; diethyl ether, dimethoxyethane, tetrahydrofuran and Ethers such as dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2- Amides such as pyrrolidone; sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; such as hexane, cyclohexane and heptane Aliphatic hydrocarbons; pyridines such as pyridine and picoline; and a mixed solvent thereof, preferably alcohols, ethers, halogenated hydrocarbons or aromatic hydrocarbons, and more preferably. Is methanol, ethanol, tetrahydrofuran, toluene or methylene chloride.

The amount of the solvent to be used is determined based on the amount of the compound (XIX)
It is generally 0.1 to 20.0 L, preferably 1.0 to 10.0 L, per 1 mol.

The reaction temperature varies depending on the starting compound, base, solvent and the like, but is usually from -10 ° C to the reflux temperature in the reaction system, preferably from 0 to 100 ° C.

The reaction time varies depending on the reaction temperature, the starting compounds, the reaction reagents and the like, but is usually from 3 minutes to 48 hours.
Preferably, it is 0.1 to 24 hours.

This step is performed, for example, in Experimental Chemistry Course No. 4
Edition (edited by The Chemical Society of Japan), 1992, Vol. 25, p. 336.

Step M Step M comprises the step of reacting the compound (IVb) with a compound of the formula (XVIII)
Is a step of producing a compound (IVc) by reacting the compound represented by the formula with a base.

Compound (XVIII) used in this step
Is usually 1.0 mol with respect to 1 mol of the compound (IVb).
To 5.0 moles, and preferably 1.0 to 3.0 moles.

The base to be used is not particularly limited as long as it generally has a pH of 8 or more. Examples thereof include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; and hydroxides of calcium hydroxide and magnesium hydroxide. Hydroxides of alkaline earth metals such as; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; sodium methoxide, sodium ethoxide and Alkoxides such as potassium tert-butoxide; hydrides of alkali metals such as sodium hydride and potassium hydride; and organic bases such as triethylamine and pyridine. When R ¹⁰ is a hydrogen atom, Preferably, alkali metal hydroxide, alkali metal charcoal A salts or organic bases, more preferably, sodium hydroxide, potassium hydroxide, sodium carbonate or triethylamine, R ¹⁰ is, C ₁
When it is a C ₆ alkylcarbonylthio group or an amidinosulfenyl group, it is preferably an alkali metal hydroxide or an alkali metal carbonate, more preferably sodium hydroxide, potassium hydroxide, sodium carbonate. Or potassium carbonate.

The amount of the base to be used is determined based on the amount of the compound (IVb)
Usually, it is 1.0 to 20.0 mol, preferably 1.0 to 10.0 mol, per 1 mol.

This step can be performed in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not hinder the reaction and dissolves the starting materials to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether, dimethoxy alcohol and the like. Ethers such as ethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone Amides; sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; acetone, methyl ethyl ketone and Ketones such as clohexanone; fatty acid carboxylic acids such as acetic acid; water; and a mixed solvent thereof, preferably alcohols, ethers or amides, more preferably methanol, ethanol. , Tetrahydrofuran or N, N-dimethylformamide.

The amount of the solvent used is determined according to the amount of the compound (IVb)
It is usually 0.05 to 20.0 L, preferably 0.1 to 10 L, per 1 mol.

The reaction temperature varies depending on the starting compound, base, solvent and the like, but is usually from 0 ° C. to the reflux temperature in the reaction system, and preferably from 10 ° C. to 100 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents, etc., but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

Step N Step N is a reaction of compound (IV) obtained by step L or M
c) is oxidized with an oxidizing agent to give the compound of the general formula (IV)
Compound represented by d) {Compound (IV) wherein n is 1 or 2. This is a step of manufacturing 、, and can be performed according to Step H.

Compound (X) which is a raw material for production in steps J to L
IV), for example, J. Phar, Journal of Pharmaceutical Sciences, 1992, 81, 181.
m. Sci., 81, 181 (1992), Chemistry of Heterocyclic Compound, 1980, Vol. 16, 47
Chem. Heterocycl.Compd., 16, 472 (1980), EP 199 281 or Organic Magnetic Resonance 1971, Vol. 3, No. 5, pp. 521-531 Org. Magn. Resonance, 3 (5) , 521-531 (197
It can be produced by the method described in 1).

Step O

[0228]

Embedded image In the formula, R ² , R ³ , R ⁴ , R ⁵ , R ^7a , A, X, m, Y and p are as defined above.

In the step O, the carbonyl compound represented by the general formula (XIX) is reacted with a hydrazine represented by the general formula (V) or a hydrate or salt thereof to give a compound (II)
This is the step of manufacturing I).

The amount of compound (V) used in this step is as follows:
Usually, from 1.0 to 10.3 mol per 1 mol of compound (XIX).
0 mol, preferably 1.0 to 5.0.

This step can be performed in the presence or absence of a solvent.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include alcohols such as methanol, ethanol, ethylene glycol and glycerin; diethyl ether, Ethers such as dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide and N Amides such as methyl-2-pyrrolidone; sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; Aliphatic hydrocarbons such as cyclohexane and heptane; pyridine and pyridines such as picoline; fatty acids such as acetic acid;
Water; and a mixed solvent thereof, preferably alcohols or ethers, more preferably alcohols, and even more preferably methanol or ethanol.

The amount of the solvent used is determined according to the amount of the compound (XIX)
It is usually 0.1 to 200.0 L, preferably 1.0 to 10.0 L, per 1 mol.

This step can be carried out in the presence or absence of an acid.

The acid to be used is not particularly limited as long as it has an ordinary pH of 6 or less. For example, mineral acids such as hydrochloric acid, sulfuric acid, perchloric acid and nitric acid; formic acid, acetic acid and propionic acid Carboxylic acids; sulfonic acids such as methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid monohydrate; acid addition salts of amines such as pyridine hydrochloride and triethylamine hydrochloride; aluminum chloride, tetrachloride Titanium, metal halides such as zinc chloride, and Lewis acids such as boron trifluoride etherate, preferably carboxylic acids or sulfonic acids.

The amount of the acid used is the same as that of compound (XIX) 1
It is usually 0.01 to 100.0 mol with respect to mol,
Preferably, it is 0.1 to 20.0 mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -10 ° C to the reflux temperature in the reaction system, preferably from 10 to 100 ° C.

The reaction time varies depending on the reaction temperature, starting compounds, reaction reagents and the like, but is usually 3 minutes to 48 hours, preferably 0.1 to 24 hours.

After completion of each of the above reaction steps, the target compound of each step can be collected from the reaction mixture by a conventional method. For example, it can be obtained by appropriately neutralizing the reaction mixture, removing any insoluble matter by filtration, adding an organic solvent immiscible with water, washing with water, and distilling off the solvent. If necessary, the obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation or chromatography.

When the compound of the present invention is used as an active ingredient of a pesticide, the compound of the present invention may be used as it is, but a carrier, a surfactant, and a carrier generally used for formulation as a pesticide adjuvant may be used. And other adjuvants, emulsions, suspensions, powders, granules, tablets, wettable powders, aqueous solvents, liquids, flowables, wettable powders, aerosols,
It can be formulated in various forms such as pastes, oils, emulsions. The proportions of these are usually 0.1 to 9.0 parts by weight of the active ingredient and 10 to 99.9 parts by weight of the pesticide adjuvant.

[0241] The carriers used in the formulation here are divided into solid carriers and liquid carriers. Examples of solid carriers include animal and plant powders such as starch, activated carbon, soybean powder, flour, wood powder, fish powder, milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, white carbon, clay, and alumina. Mineral powder. Examples of the liquid carrier include water, alcohols such as isopropyl alcohol and ethylene glycol, ketones such as cyclohexane and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, kerosene, aliphatic hydrocarbons such as light oil, and xylene. Aromatic hydrocarbons such as trimethylbenzene, tetramethylbenzenemethylnaphthalene, solvent naphtha, halogenated hydrocarbons such as chlorobenzene, acid amides such as dimethylacetamide, esters such as glycerin ester of fatty acid, Nitriles such as acetonitrile and sulfur-containing compounds such as dimethyl sulfoxide.

Examples of the surfactant include metal salts of alkyl benzene sulfonic acid, metal salts of dinaphthyl methane disulfonic acid, alcohol sulfates, alkyl aryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers and polyoxyethylene alkyls. Aryl ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned.

Other adjuvants include, for example, fixing agents or thickeners such as carboxydimethylcellulose, gum arabic, sodium alginate, guar gum, tragacanth gum, polyvinyl alcohol, defoaming agents such as metal soaps, fatty acids, alkyls Phosphates, silicones,
A physical property enhancer coloring agent such as paraffin can be used.

In the actual use of these preparations, they can be used as they are, or can be used after being diluted to a predetermined concentration with a diluent such as water. The application of various preparations containing the compound of the present invention, or a diluent thereof, is usually carried out by a general application method, ie, spraying (eg, spraying, misting, atomizing, dusting, dusting, water surface) Application, box application, etc.), soil application (for example, mixing, irrigation, etc.), surface application (for example, application, dressing, coating, etc.), immersion, bait and the like can be performed. Further, it is also possible to control the occurrence and growth of harmful insects, especially harmful insects, in their excrement by giving the active ingredient to the livestock mixed with the material. It can also be applied by a so-called ultra-high concentration small amount spraying method. In this method, it is possible to contain 100% of the active ingredient.

The application of the pesticidal composition of the present invention is generally 0.1 to 50000 ppm, preferably 1 to 1000 ppm.
The test is performed at an active ingredient concentration of 0 ppm.

The concentration of the active ingredient can be appropriately changed depending on the form of the preparation and the method, purpose, timing, place and pest occurrence of the pest. For example, in the case of aquatic pests, even if a chemical solution having the above concentration range is sprayed at the place of occurrence, control can be achieved. 0.1 to 5000 as active compound per unit area
g, preferably 1 to 1000 g, is not limited thereto.

Needless to say, the compound of the present invention is sufficiently effective alone, but if necessary, other fertilizers and pesticides such as insecticides, acaricides, nematicides, fungicides, antibacterial agents, It can be mixed and used in combination with a virus agent, an attractant, a herbicide, a plant regulator, and the like, and in this case, an even better effect may be exhibited.

Representative examples of insecticides, fungicides and acaricides which can be used in combination with the compound of the present invention are shown below.

Examples of the organic phosphorus and carbamate insecticides include fenthion, fenitrothion, diazinon,
Chloropyrifos, oxydephos, bamidione, fentoate, dimethoate, formotion, malathion, trichlorofon, thiomethone, phosmet, dichlorophos, acephate, EPBP, methylparathion,
Oxydimetone methyl, ethion, dioxabenzophos, cyanofos, isoxathion, pyridafenthion, hosalon, methidathion, sulfophos, chlorofenvinphos, tetrachlorovinphos, dimethylvinphos, propaphos, isofenphos, disulfoton, propenophos, pyraclophos, monocrotophos, Azinphosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, carbosulfan, benfracarb, flatiothiocarb, propoxur, fenobcarb, metolcarb, isoprocarb, carbaryl, pirimicarb, ethiophencarb, diclofenthione, pirimiphosmethyl, quinalphos, chloropyrifosmethyl, prothiophos, X, Nared , Bendiocarb, oxamil, alanical , Chloroethoxy phosphate and the like.

Examples of the pyrethroid insecticides include permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, allethrin,
Tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprothrin, tralomethrin,
Silafluofen, tefluthrin, bifenthrin, acrinatrine and the like.

Other insecticides include diflubenzuron, chlorofluazuron, hexaflumuron, triflumuron, teflubenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, lufenuron, cyromazine, methoprene, endosulfan, diafenthiu Ron, imidaproclide, fipronil, phenoxycarb, cartap, thiocyclam, bensultap, tebufenozide, chlorofenapyr, emamectin benzoate, acetamiprid, nitenpyram, pymetrozine, sodium oleate, nicotine sulfate, rotenone, methenaldehyde, machine oil, rapeseed oil, BT agent, BT agent Microbial pesticides such as entomopathogenic viruses.

Examples of nematicides include phenamiphos, phosthiazate, etopropos, methyl isothiocyanate,
1,3-dichloropropene, DCIP and the like.

As acaricides, chlorobenzylate,
Phenisobromolate, dicofol, amitraz, propargite, benzomate, hexthiazox, fenbutatin oxide, polynactin, quinomethionate,
Examples include chlorophenson, tetradiphone, abamectin, milbemectin, clofenthedine, pyridaben, fenpyroximate, tebufenpyrad, pyrimidifen, phenothiocarb, dienochloro, ethoxazole, and halfenprox.

As bactericides, thiophanate methyl,
Benomyl, carbendazole, thiabendazole, phorbet, thiuram, ziram, zineb, maneb, manzeb, polycarbamate, iprovenphos, edifenfos, fusaride, probenazole, isoprothiolane, chlorothalonil, captan, polyoxin, blasticidin S, kasugamycin, streptomycin, Validamycin, tricyclazole, pyroquilon,
Phenazine oxide, mepronil, flutranyl, pencyclone, iprodione, himexazole, metalaxyl, triflumizole, triforine, triadimefon,
Bitertanol, fenarimol, propiconazole, simoxanil, polochloraz, pefurazoate, hexaconazole, microbutanyl, diclomedine, teclophthalam, propineb, dithianone, fosetyl, vinclozolin, procymidone, oxadixil, guazatine, propamocarbic acid, fluazinam, fluazinam Sol, imibenconazole,
And mepanipyrim.

The compounds of the present invention can be used as a pest of the order Hemiptera, Lepidoptera, Coleoptera, Sophora, Hymenoptera, Orthoptera, Termites, Thrips, Spider mites, Plant parasitic It shows an excellent control effect against pests such as nematodes. Examples of such pests include the following pests.

As the pests of the order Hemiptera, for example, Riptortus clavatas, southern stink bug (Nezara viridul)
a), the stink bug (Lygus sp.), the American bug stink bug (Blissus leucp)
terus), Nashigumbai (Stephanitis)
sting bugs (Hetera; HRTER)
OPTERA), leafhopper (Nephotet)
ix cincticeps), leafhopper (Em)
poasca sp. , Erythroneura
sp. , Circifer sp. ), Leafhoppers (Nilaparvata)
lugens), Scotch planthopper (Sogatalla)
furcifera) and Japanese brown planthopper (Laodel)
planthoppers such as P. physalisatellas, Psylla sp. Lice such as lice, Bemisia tabaci, Trifolium lice (Trialeurodes vapor)
whiteflies (Ariorum), whiteflies such as Aphiorum aphid, Aphis pomii, Aphis gossypii, Aphis gossypii, Aphis pomphi, Aphis gossypii
abae, radish aphids (Rhopalos)
iphum psedobrassicas, potato beetle aphid (Aulacorthum s)
olani), wheat midori aphid (Schizap)
aphids such as his graminum, and Pseudococcus co.
mstocki), Ruby beetle (Ceroplas)
tes rubens), San Jose scale insect (C)
omstockaspis perniciosa),
Unapsi yanoens
is) and scale turtles (Rhodni)
us sp. ) And the like.

As the lepidopteran pests, for example, Chahamaki (Homona magnanima), Kokumakumamaki (Adoxophyes orana), Staghamaki (Sparganothis pilarian)
a), Nasihime Shingui (Grapholitham)
olesta), Mameshin iga (Leguminiv)
ora glycinivorella), codling moth (Laspeyresia pomonella), E
ucosma sp. , Lobesia botran
A toad, such as a
Ciliaambiguella), such as Bombalina sp. Species such as Nemopogon granellalu
s), rainbow trout moths such as iga (Tinea translucens), lycopodium (Lyone)
Leaf moths such as tiapunifoliela, Phyllonoryctor
rigoniella), and the citrus leaf moth (Phyllocnistis citrel).
laminating moth moths, such as the moth moth (Plutel)
la xylostella), Plays citr
Suga like i, grape squash (Paranthr)
ene regalis), Synanthendon
sp. Scabbards, such as cotton beetle (Pect
inophora gossypiella, potato moth (Phothomaea operculelle)
la), Stopteryx sp. Mosquitoes such as peach, peach sinker (Carposina nipo)
sink moth such as Nensis, Iraga (Mon)
ema flavescens), Iriga, Chilosuppressalis, Cnapalocrocismedin
alis), Ostrinia nubilalis,
Awanomeiga (Ostrinia furnacali)
s), Himuradanomeiga (Hellula unda)
lis) Honey (Galleria mellon)
ella), Elasmopalpus lignos
ellus, Loxostege scientific
scabbard moths such as is, the white butterfly (Pieris
white butterflies such as Rapae, Paeonia such as Ascotis selenaria, and Malakosomaneust.
ria), such as the Mandarina sex, Manduca sex
spiders such as ta,
is pseudoconspersa, Lymantria dispar, etc., Hyphantria cu
Triggers such as nea), tobacco badworm (H
elioth virescens), ball worm (Helikoverpa zea), armyworm (Spodoptera exigua), and giant tobacco armyworm (helicoverpa armiger)
a), Spodoptera lit
ura), armyworm (Mamestra brassi)
cae), Tamana yaga (Agrotis ipsiro)
n), armyworm (Pseudoletia sepa)
rata), nettle (Tchocholu)
and nodules such as sia ni).

Examples of the insects of the order Coleoptera include, for example, Anemona cuprea, Bean beetle (Popillia japonica), Anisela rufocuprea, and Euth.
beetles such as eolalugiceps, wire worms (Agricotes sp.), Cono
deus sp. Beetles, such as the beetle (Epilachna vitintio)
ctopuncta), ladybird (E
ladybirds such as pilachna varivestis, and Tribolium
beetles, such as C. castaneum, and Anoplophora malasi
aca), Matsunomadami beetle (Monochamu)
longhorn beetles, such as
Bean weevil (Acanthoscelide)
sobectus), Adzuki beetle (Callos)
beetles, such as L. obtruchus chinensis, and the leaf beetle (Leptinotars).
a declineinea), corn rootworm (Diabrotica sp.), rice beetle (Olema oryzae), tenet beetle (Chaeocnema concinna), Ph
aedoncochlearias, Olemmam
elanopus, Diclatispa armig
beetles such as era, Apion Godmani
Weevil, rice weevil (Li
ssorhoptrusoryzophilus, cotton weevil (Anthonomus grandi)
weevil such as weevil, Sitoph
weevil, such as ilus Zeamais)
Bark beetles, beetles, beetles and the like.

Examples of the dipteran insect pests include, for example, Killer crab (Tipra ano) and rice chironomid (Tan
ytarsus oryzae, rice scintillation fly (Orseolia oryzae), medfly (Ceratitiscapitata), and rice fly (Hydrellia griseol)
a), Drosophila (Drosophil)
a suzukii), Fritz fries (Oscine)
lla frit), rice flies (Chlorops)
oryzae), haricot fly (Ophiom)
yia phaseoli)
riomyza trifolii, Pegomya hyoscyami, Fly (Hylemia platura), Sorghum (Atherigona soccata), Housefly (Musca domoepsia, Musca domoepsia).
tomoxys sp. ), Aedes aegypti (Aede)
s aegypti), Culex pipiens (Culex pi)
piens), Anopheles
slnensis), Culex pipiens (Culex)
tritaeniorhynchus) and the like. .

Examples of the hymenoptera pests include, but are not limited to, wasps (Cephus sp.), And honey bees (Harm).
olita sp. ), Alaska bee (Athalia)
sp. ), Hornets (Vespa sp.), Fire ants and the like.

As the pests of the order Orthoptera, for example, German cockroaches (Blatella germanica) and cockroaches (Periplaneta americic)
ana), Kera (Grylotalpa afric)
ana), grasshopper (Locusta migrator)
ia migratriodes), Melanop
rus sanguinipes and the like.

Examples of the thrips pests include, for example, Thrips thrips doi
rsalis, Thrips palmi (Thrip)
spalmi), Croton thrips (Helioth)
rips haemorrhoidalis, Citrus thrips (Frankliniellaoc)
identalis), Thrips palmi (Hapl)
otripsaculeatus) and the like.

As the spider mites, for example, spider mites (Tetranychus urticae) and Kanzawa spider mites (Tetranychus kanzawa)
i) Citrus red mite (Panonychus citr)
i) Apple spider mite (Panonychus ulm)
i), yellow mites (Eotetranychus)
carpini), Texas Citrus Mite (Eote)
tranychus banki), citrus red mite (Phylocoptrutta oleivor)
a), Polyphagotars
onemus latus, Broom spider mite (Brevi)
palpus sp. ), Robin mite (Rhizog)
lyphus robini), Scarlet mite (Tyr)
ophagus putresentiae).

As the plant parasitic nematodes, for example, sweet potato nematodes (Meloidogyne i)
ncognita), Negusaresenchu (Praty)
lenchus sp. ) Soy cyst nematode (H
eterodera glycines), Ashingenchoides bes
seyi), pine wood nematode (Bursaphe)
enchus xylophilus) and the like.

Other pests, unpleasant animals, sanitary pests and parasites include, for example, Scrimming mussels (Poma
sea canaliculata, slugs (In
ciaria sp. ), African Maimai (Ach
Gastropods (Gas) such as atina fulica
tropoda), Armadillid (Armadillid)
ium sp. ), Isopoda, such as Coleoptera, Centipede, Liposcelis sp.
Beetles, such as Ctenolepisma
sp. Stains such as Pulex sp. , Cten
ocephalides sp. Fleas such as Tr
ichodictes sp. Lice like C, C
imex sp. Lice such as bed bug, tick (Boophilus microplus), tick (Haemaphysalis longi)
cornis), Dermatophagoides and the like.

Furthermore, it is also effective against pests that are resistant to organic phosphorus compounds, carbamate compounds, synthetic pyrethroid compounds, acylurea compounds, or existing insecticides.

Hereinafter, the compound of the present invention will be specifically described with reference to Examples, Preparation Examples and Test Examples, but the present invention is not limited thereto.

[0268]

【Example】

[0269]

Example 1 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-methoxycarbonylhydrazone (Compound No. 1-344) (Step A) Obtained according to Example 8 (3) below. 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone (0.65 g) and methyl carbazate (1.27)
g) was added to ethanol (15 ml) and acetic acid (16 ml), and the mixture was stirred under reflux for 8 hours. The reaction mixture was poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 5 /
1) to give the title compound (0.44 g, yield 54)
%). Physical properties: Oil Mass spectrum (EI) m / e: 368 (M ⁺ ) ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.63, 8.3
1 (1H, brd.s), 7.51-7.61 (2H, m), 7.23-7.33 (2H, m),
6.76, 7.05 (1H, d, d, J = 3.6, 3.6Hz), 6.56, 7.02 (1H,
d, d, J = 3.6, 3.6Hz), 3.87, 3.96 (2H, s, s), 2.81,
3.85 (3H, s, s), 1.53, 2.60 (2H, q, q, J = 7.4, 7.4Hz),
1.24, 1.29 (3H, t, t, J = 7.4, 7.4Hz).

[0270]

Example 2 4-chlorophenyl 5-methylthiomethylthiophen-2-yl ketone hydrazone (Compound No. 1-1) (Step A) 4-chlorophenyl obtained according to Example 8 (3) below 5-Methylthiomethylthiophen-2-yl ketone (11.92 g) and hydrazine monohydrate (6.40)
g) was added to ethanol (50 ml) and acetic acid (3 ml), and the mixture was stirred under reflux for 5 hours. Pour the reaction mixture into water,
Extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane / ethyl acetate = 7/1) to obtain the title compound (10.98 g, yield 88%). Physical properties: solid Mass spectrum (EI) m / e: 296 (M ⁺ ) ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.44-7.53
(2H, m), 7.26-7.34 (2H, m), 6.73, 7.03 (1H, d, d, J =
3.6, 3.6Hz), 6.41, 6.99 (1H, d, d, J = 3.6, 3.6Hz),
5.32, 5.85 (2H, brd.s, brd.s), 3.82, 3.92 (2H, s,
s), 2.09, 2.14 (3H, s, s).

[0271]

Example 3 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N-acetylhydrazone (Compound No. 1-2) (Step E) 4 obtained according to Example 8 (3) below. -Chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = hydrazone (100 mg), acetyl chloride (30 m
g) and potassium carbonate (63 mg) in ethyl acetate (1.
5 ml) and water (1.0 ml), and the mixture was stirred at room temperature for 3 hours. Further, ethyl acetate (30 ml) was added, washed with saturated aqueous sodium hydrogen carbonate and saturated saline, dried over magnesium sulfate and concentrated, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 1/5).
To give the title compound (109.5 mg, yield 85.0).
%). Physical properties: solid Mass spectrum (EI) m / e: 338 (M ⁺ ), 291, 249, 184 ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.19, 8.8
0 (1H, s, s), 7.49-7.59 (2H, m), 7.22-7.59 (2H, m),
6.77, 7.03 (1H, d, d, J = 3.7, 3.7Hz), 6.55, 6.98 (1H,
d, d, J = 3.7, 3.7Hz), 3.84, 3.91 (2H, s, s), 2.38,
2.42 (3H, s, s), 2.11, 2.15 (3H, s, s).

[0272]

Example 4 4-Chlorophenyl 5-ethylsulfinylmethylthiophen-2-yl ketone N-methoxycarbonylhydrazone (Compound No. 1-345) (Step H) 4-chlorophenyl obtained according to the above Example 1. Chlorophenyl = 5
-Methylthiomethylthiophen-2-yl = ketone = N
-Methoxycarbonylhydrazone (162.4 mg) and 3-chloroperbenzoic acid (83.3 mg) were added to 1,2-dichloroethane (3 ml), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by thin-layer silica gel chromatography (elution solvent: methylene chloride / methanol = 10/1) to give the title compound (145.3 mg, yield 85%). Physical properties: solid Mass spectrum (EI) m / e: 384 (M ⁺ ) ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.69, 8.3
5 (1H, brd.s, brd.s), 7.53-7.57 (2H, m), 7.24-7.33 (2
H, m), 6.89, 7.20 (1H, d, d, J = 3.6, 3.6Hz), 6.66,
7.13 (1H, d, d, J = 3.6, 3.6Hz), 4.08-4.29 (2H, m), 3.
81, 3.84 (3H, s, s), 2.51, 2.59 (3H, s, s).

[0273]

Example 5 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = [N '-(ethoxycarbonyl) methylidene] hydrazone (Compound No. 1-
101) (Step F) 4-chlorophenyl = 5 obtained according to Example 2 above
-Methylthiomethylthiophen-2-yl ketone = hydrazone (122.1 mg) and ethyl glyoxylate (135.3 mg) were added to ethanol (2 ml), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by thin-layer silica gel chromatography (elution solvent: hexane / ethyl acetate = 4/1) to give the title compound (112.2 mg, yield 72%). Physical properties: Oil Mass spectrum (EI) m / e: 380 (M ⁺ ) ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.76, 7.8
3 (1H, s, s), 7.27-7.61 (4H, m), 6.94, 7.13 (1H, d,
d, J = 3.8, 3.8Hz), 6.88, 6.95 (1H, d, d, J = 3.8,3.8H
z), 4.29, 4.44 (2H, q, q, J = 7.2, 7.2Hz), 3.87, 3.90
(2H, s, s), 2.11,2.13 (3H, s, s), 1.31, 1.44 (3H, t,
t, J = 7.2, 7.2Hz).

[0274]

Example 6 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N-ethoxycarbonyl-N-methoxymethylhydrazone (Compound No. 1-)
131) (Step E) 4-chlorophenyl = 5 obtained according to Example 1 above
-Methylthiomethylthiophen-2-yl = ketone = N
-Ethoxycarbonylhydrazone (100 mg) with N,
Dissolve in N-dimethylformamide (2 ml), add sodium hydride (60% mineral oil, 48 mg) under ice cooling, stir for 15 minutes, add methoxymethyl chloride (30 mg), and stir under ice cooling for 1 hour did. Ethyl acetate (30 ml) was added, washed with saturated saline, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (elution solvent: hexane / ethyl acetate = 1/5) to give the title compound (222). 0.7 mg, yield 55.8%). Physical properties: Solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.58 (2H,
d, J = 8.7Hz), 7.40 (2H, d, J = 8.7Hz), 7.01 (1H, d, J = 3.
8Hz), 6.89 (1H, d, J = 3.8Hz), 5.04 (2H, s), 3.87 (2H,
s), 3.69 (3H, s), 3.47 (3H, s), 2.10 (3H, s).

[0275]

Example 7 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N '-[1
-(N-ethylamino) ethylidene] hydrazone (Compound No. 1-242) (Step G) 4-chlorophenyl = 5 obtained according to Example 1 above
-Methylsulfonylmethylthiophen-2-yl = ketone = N-acetylhydrazone (105.6 mg), triphenylphosphine (183.1 mg) and carbon tetrachloride (260 μl) were added to acetonitrile (3 ml) and refluxed for 30 minutes. Stirred for minutes. After returning to room temperature, a 3.18 M toluene solution (260 μl) of ethylamine was added, and
Stirred for hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by thin-layer silica gel chromatography (elution solvent: hexane / ethyl acetate = 1/2), and the title compound was found to have an Rf value of 0.6 (50.5 mg, yield 45%).
And those having an Rf value of 0.5 (27.2 mg, yield 24
%). The title compound physical properties of Rf value 0.6: oil MASS de - data (EI) m / e: 397 (M +), 318, 249, 235. 1 H-NMR (200MHz, CDCl 3) spectrum [delta] (ppm) ： 7.60-6.73
(6H, m), 6.72-6.43 (1H, m), 4.47, 4.46 (2H, s, s),
3.70-3.24 (2H, m), 2.85, 2.83 (3H, s, s), 2.26, 2.2
5 (3H, s, s), 1.35, 1.21 (3H, t, t, J = 7.2, 7.2 Hz). The title compound having an Rf value of 0.5 Physical properties: Oil MASS data (EI) m / e: ^{397 (M +), 318,} 249, 235. 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 7.84-7.33
(4.4H, m), 7.10-7.08 (0.8H, m), 7.02 (0.6H, d, J =
3.9Hz), 6.76 (0.6H, d, J = 3.8Hz), 6.53-6.33 (0.6H,
m), 4.50-4.40 (2H, m), 3.70-3.55 (0.4H, m), 3.38-
3.24 (1.2H, m), 3.21-3.08 (0.4H, m), 2.89, 2.87,
2.85, 2.83 (3H, s, s, s, s), 2.25, 2.24,2.21, 1.99
(3H, s, s, s, s), 1.38-1.04 (3H, m).

[0276]

Example 8 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone (Compound No. 3-1)
(Step K and Step M) (1) 4-chlorophenyl-5-bromomethylthiophen-2-yl = ketone 4-chlorophenyl = 5-methylthiophen-2 produced according to the method described in EP 199281. -Il-ketone (36.7 g) in carbon tetrachloride solution (500 ml) was added to N-bromosuccinimide (92.
6 g) was added, and the mixture was heated under reflux for 9 hours. After the reaction solution was cooled to room temperature and filtered, the solid on the filter paper was washed with methylene chloride. The filtrate and washing solution were combined, washed with water and saturated saline, and dried using magnesium sulfate. The solvent was distilled off, and the residue was washed with diethyl ether and filtered to obtain 4-chlorophenyl-5-bromomethylthiophen-2-yl) ketone (45.05 g, yield 92.1%). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.81 (2H,
d, J = 8.8Hz), 7.51-7.46 (3H, m), 7.17 (1H, d, J = 3.6H
z), 4.71 (2H, s). (2) 4-chlorophenyl-5-amidinosulfenylmethylthiophen-2-yl ketone 4-chlorophenyl-5-bromomethylthiophen-2-yl obtained in (1) = To a solution of ketone (3.16 g) in acetone (50 ml) was added thiourea (1.01 g), and the mixture was heated under reflux for 3 hours. The precipitated crystals were collected by filtration, washed with acetone, and washed with 4-chlorophenyl-5-amidinosulfenylmethylthiophen-2-yl = ketone (3.1
5g, 80.3% yield). Melting point: 205-207 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.35-9.1
(3H, m), 7.86 (2H, d, J = 8.6Hz), 7.68-7.64 (3H, m),
7.29 (1H, d, J = 3.8 Hz), 4.87 (2H, s). (3) 4-chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone 4-chlorophenyl obtained from (2) = 5- Amidinosulfenylmethylthiophen-2-yl ketone (1.
01g) and methyl iodide (0.32 ml).
Potassium carbonate (0.43 g) was added to a dimethylformamide (10 ml) solution, and the mixture was stirred at room temperature for 10 minutes.
Thereafter, a methanol solution (6 ml) of potassium hydroxide (0.28 g) was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into saturated saline and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate.
After evaporating the solvent, the crude product was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 10/1).
And purified with the title compound (0.56 g, yield 76.7).
%). Melting point: 77-78 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.81 (2H,
d, J = 8.6Hz), 7.47 (2H, d, J = 8.6Hz), 7.48 (1H, d, J = 3.
8Hz), 7.02 (1H, d, J = 3.8Hz), 3.91 (2H, s), 2.13 (3H,
s).

[0277]

Example 9 4-chlorophenyl = 2,2,2-trifluoroethylthiomethylthiophen-2-yl = ketone (Compound No. 3-9) (Step L) 2,2,2-trifluoroethyl mercaptan (1) .0
Sodium hydride (60% mineral oil, 0.35 g) was added to a mixed solution of 0 g) of N, N-dimethylformamide (3 ml) -tetrahydrofuran (12 ml) at 0 ° C.
The mixture was stirred at 30 ° C for 30 minutes and at room temperature for 30 minutes. 4-chlorophenyl-5-bromomethylthiophen-2-yl ketone (2.47 g) obtained in Example 8 (1) was added to
C. and stirred at room temperature for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the crude product was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 10/1) to obtain the title compound (1.40 g, yield 60.0%). Physical properties: Oil Mass spectrum (EI) m / e: 364 (M ⁺ ) ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.81 (2H,
d, J = 8.6Hz), 7.52-7.46 (3H, m), 7.05 (1H, d, J = 3.8H
z), 4.08 (2H, s), 3.09 (2H, q, J = 9.8Hz).

[0278]

Example 10 4-chlorophenyl-5-methanesulfonylmethylthiophen-2-yl ketone (Compound No. 3-3) (Step J) Sodium sulfite (26.40 g) and sodium hydrogen carbonate (33.0 g) were added to water. (200 ml), methanesulfonyl chloride (22.00 g) was added to this solution at room temperature for 30 minutes, and the mixture was stirred for 2 hours. The reaction mixture was concentrated, azeotroped with toluene and dried. The obtained residue is washed with N, N-dimethylformamide (200 m
After suspending in 1), 4-chlorophenyl-5-bromomethylthiophen-2-yl = ketone (12.05 g) obtained in Example 8 (1) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into saturated saline and extracted with ethyl acetate. Further, the organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained residue was washed with a diethyl ether-hexane mixed solvent (diethyl ether / hexane = 1/10) to obtain the title compound (10.48 g, yield 87.2%). Melting point: 149-151 ° C. Mass spectrum (EI) m / e: 314 (M ⁺ ) ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.82 (2H,
d, J = 8.6Hz), 7.58 (1H, d, J = 4.0Hz), 7.50 (2H, d, J = 9.
0Hz), 7.28 (1H, d, J = 4.0Hz), 4.50 (2H, s), 2.92 (3H,
s).

[0279]

Example 11 4-chlorophenyl 4-ethylthiomethylthiophen-2-yl ketone (Compound No. 4-
3) (Step L) (1) 4-chlorophenyl-4-chloromethylthiophen-2-yl = ketone chemistry of heterocyclic compound 1980 Vol. 16 No. 4 3
AIB was added to a solution of 4-chlorophenyl 4-methylthiophen-2-yl ketone (355 mg) in benzene (5 ml) obtained according to the method described on pages 56 to 358.
N (25 mg) and sulfuryl chloride (405 mg) were added, and the mixture was stirred for 5 hours. The reaction mixture was cooled to room temperature, ethyl acetate (30 ml) was added, and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and then with a saturated saline solution, dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure.
The residue was subjected to thin-layer silica gel chromatography (developing solvent:
Purification with hexane / ethyl acetate = 30/1) gave 4-chlorophenyl-4-chloromethylthiophen-2-yl) ketone (207.5 mg, yield 51%). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.83 (2H,
d, J = 8.6Hz), 7.68 (1H, d, J = 1.3Hz), 7.62 (1H, d, J = 1.
3 Hz), 7.50 (2H, d, J = 8.6 Hz), 4.60 (2H, s). (2) 4-chlorophenyl-4-ethylthiomethylthiophen-2-yl = ketone Sodium hydride (60% mineral oil, 37 mg) ) To N, N-
0 ° C while suspended in dimethylformamide (2 ml)
Then, ethyl mercaptan (57 mg) was added thereto, followed by stirring for 15 minutes. 4-Chlorophenyl 4-chloromethylthiophen-2-yl ketone (207 mg) was added thereto, and the mixture was stirred at 0 ° C for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate (30ml). The organic layer was washed with brine and dried over anhydrous magnesium sulfate.
After evaporating the solvent, the obtained residue was subjected to a mixed solvent of diethyl ether-hexane (diethyl ether / hexane = 1/1).
0) and washed with the title compound (10.48 g, yield 8).
7.2%). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.82 (2H,
d, J = 8.6Hz), 7.59 (1H, d, J = 1.4Hz), 7.48 (2H, d, J = 8.
6Hz), 7.46 (2H, d, J = 1.4Hz), 3.73 (2H, s), 2.47 (2H,
q, J = 7.4Hz), 1.24 (3H, t, J = 7.4Hz).

[0280]

Example 12 4-Chlorophenyl 4-ethylthiomethylthiophen-2-yl ketone N-methoxycarbonylhydrazone (Compound No. 2-9) (Step A) 4-Chlorophenyl 4-ethylthiomethylthiophen-2 -Yl = ketone (119.8 mg) and methyl-carbazate (193.7 mg) in ethanol (3 ml)
And acetic acid (1 ml), and the mixture was stirred under reflux for 10 hours. The reaction mixture was poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The residue was purified by thin-layer silica gel chromatography (eluent: hexane / ethyl acetate = 3/1) to give the title compound (8
7.0 mg, 59% yield). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.65, 8.2
6 (1H, brd.s, brd.s), 7.52-7.59 (2H, m), 7.25-7.33 (2
H, m), 7.14, 7.39 (1H, s, s), 6.74, 7.13 (1H, s, s),
3.82, 3.86 (3H, s, s), 3.59, 3.78 (2H, s, s), 2.41,
2.53 (2H, q, q, J = 7.4, 7.4Hz), 1.19, 1.28 (3H, t, t,
J = 7.4, 7.4 Hz). The following compounds were produced according to Examples 1 to 12 above.

[0281]

Example 13 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-propionylhydrazone (Compound No. 1-3) Physical properties: solid Mass spectrum (EI) m / e: 352 (M ⁺ ), ^{305, 249. 1 H-NMR (} 200MHz, CDCl 3) spectrum δ (ppm): 8.18 (1H ,
s), 7.54 (2H, d, J = 8.4Hz), 7.27 (2H, d, J = 8.4Hz), 6.
77 (1H, d, J = 3.7Hz), 6.34 (1H, d, J = 3.7Hz), 3.84 (2H,
s), 2.79 (2H, q, J = 7.5Hz), 2.11 (3H, s), 1.21 (3H,
t, J = 7.5Hz).

[0282]

Example 14 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-butyrylhydrazone (Compound No. 1-4) Physical properties: solid Mass spectrum (EI) m / e: 366 (M ⁺ ) ^{, 319, 249. 1 H-NMR} (200MHz, CDCl 3) spectrum δ (ppm): 8.12, 8.7
9 (1H, s, s), 7.51-7.61 (2H, m), 7.22-7.37 (2H, m),
6.77, 7.04 (1H, d, d, J = 3.7, 3.7Hz), 6.54, 6.99 (1H,
d, d, J = 3.7, 3.7Hz), 3.83, 3.91 (2H, s, s), 2.70-
2.84 (2H, m), 2.11,2.16 (3H, s, s), 1.68-1.84 (2H,
m), 1.04 (3H, t, J = 7.4Hz).

[0283]

Example 15 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-isobutyrylhydrazone (Compound No. 1-5) Melting point: 124-125 ° C. Mass spectrum (EI) m / e: 366 ^{(M +), 319, 249.} 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.16 (1H ,
s), 7.54 (2H, d, J = 8.4Hz), 7.27 (2H, d, J = 8.4Hz), 6.
77 (1H, d, J = 3.7Hz), 6.54 (1H, d, J = 3.7Hz), 3.85 (2H,
s), 3.49 (1H, quintet, J = 6.9Hz), 2.11 (3H, s), 1.23
(6H, d, J = 6.9Hz).

[0284]

Example 16 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-valerylhydrazone (Compound No. 1-6) Physical properties: solid Mass spectrum (EI) m / e: 380 (M ⁺ ) ^{, 333, 293, 249. 1 H} -NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.17, 8.7
7 (1H, s, s), 7.49-7.60 (2H, m), 7.23-7.39 (2H, m),
6.77, 7.04 (1H, d, d, J = 3.7, 3.7Hz), 6.54, 6.97 (1H,
d, d, J = 3.7, 3.7Hz), 3.85, 3.92 (2H, s, s), 2.71-
2.87 (2H, m), 2.11,2.16 (3H, s, s), 1.25-1.80 (4H,
m), 0.98 (3H, t, J = 7.3Hz).

[0285]

Example 17 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-octanoylhydrazone (Compound No. 1-13) Physical properties: solid Mass spectrum (EI) m / e: 422 (M ⁺ ) ^{, 375, 296, 249. 1 H} -NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.17 (1H ,
s), 7.53 (2H, d, J = 8.5Hz), 7.26 (2H, d, J = 8.5Hz), 6.
77 (1H, d, J = 3.7Hz), 6.54 (1H, d, J = 3.7Hz), 3.85 (2H,
s), 2.76 (2H, t, J = 7.3Hz), 2.11 (3H, s), 1.63-1.80
(2H, m), 1.21-1.50 (8H, m), 0.89 (3H, s).

[0286]

Example 18 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N-decanoylhydrazone (Compound No. 1-15) Physical properties: solid Mass spectrum (EI) m / e: 450 (M ⁺ ) ^{, 403, 296, 249. 1 H} -NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.17, 8.6
9 (1H, s, s), 7.48-7.59 (2H, m), 7.21-7.37 (2H, m),
6.77, 7.04 (1H, d, d, J = 3.7, 3.7Hz), 6.54, 6.97 (1H,
d, d, J = 3.7, 3.7Hz), 3.83, 3.91 (2H, s, s), 2.11,
2.16 (3H, s, s), 1.62-1.81 (2H, m), 1.17-1.51 (14H,
m), 0.83-0.95 (3H, m).

[0287]

Example 19 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-cyclopropylcarbonylhydrazone (Compound No. 1-16) Physical properties: solid Mass spectrum (EI) m / e: 364 (M ^{+ .), 317, 249 1 H} -NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.30, 8.9
0 (1H, s, s), 7.26-7.63 (2H, m), 6.77, 7.05 (1H, d,
d, J = 3.3, 3.3Hz), 6.55, 7.00 (1H, d, d, J = 3.3,3.3H
z), 3.85, 3.92 (2H, s, s), 2.72-2.85 (1H, m), 2.10,
2.16 (3H, s, s), 0.90-1.26 (4H, m).

[0288]

Example 20 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-cyclobutylhydrazone (Compound No. 1-17) Physical properties: solid Mass spectrum (EI) m / e: 378 (M ⁺ ) ^{, 331, 249. 1 H-NMR} (200MHz, CDCl 3) spectrum δ (ppm): 8.12 (1H ,
s), 7.53 (2H, d, J = 7.6Hz), 7.25 (2H, d, J = 7.6Hz), 6.
76 (1H, d, J = 3.7Hz), 6.52 (1H, d, J = 3.7Hz), 3.80-3.9
8 (3H, m), 1.82-5.49 (9H, m).

[0289]

Example 21 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-cyclopentylhydrazone (Compound No. 1-18) Physical properties: solid Mass spectrum (EI) m / e: 392 (M ⁺ ), ^{345, 249. 1 H-NMR (} 200MHz, CDCl 3) spectrum δ (ppm): 8.16, 8.7
6 (1H, s, s), 7.49-7.61 (2H, m), 7.22-7.38 (2H, m),
6.77, 7.04 (1H, d, d, J = 3.7, 3.7Hz), 6.53, 6.98 (1H,
d, d, J = 3.7, 3.7Hz), 3.85, 3.92 (2H, s, s), 3.49-
3.69 (1H, m), 2.11,2.16 (3H, s, s), 1.59-2.10 (8H,
m).

[0290]

Example 22 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N-cyclohexylhydrazone (Compound No. 1-19) Physical properties: solid Mass spectrum (EI) m / e: 406 (M ^{+ ), 359, 296, 249. 1} H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.10, 8.6
9 (1H, s, s), 7.49-7.62 (2H, m), 7.21-7.39 (2H, m),
6.77, 7.04 (1H, d, d, J = 3.7, 3.7Hz), 6.54, 6.97 (1H,
d, d, J = 3.7, 3.7Hz), 3.85, 3.92 (2H, s, s), 3.14-
3.41 (1H, m), 1.18-2.19 (13H, m).

[0291]

Example 23 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N-acryloylhydrazone (Compound No. 1-20) Physical properties: solid Mass spectrum (EI) m / e: 350 (M ⁺ ), ^{303, 249. 1 H-NMR (} 200MHz, CDCl 3) spectrum δ (ppm): 8.29, 8.8
9 (1H, s, s), 7.52-7.67 (2H, m), 7.21-7.41 (2H, m),
6.77, 7.04 (1H, d, d, J = 3.7, 3.7Hz), 7.01 (2H, m), 6.
48-6.63 (2H, m), 5.90 (1H, m), 3.85, 3.92 (2H, s, s),
2.11, 2.16 (3H, s, s).

[0292]

Example 24 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-methoxyacetylhydrazone (Compound No. 1-31) Physical properties: solid Mass spectrum (EI) m / e: 368 (M ⁺ ) . ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.21, 9.1
9 (1H, s, s), 7.51-7.69 (2H, m), 7.21-7.40 (2H, m),
6.57-7.10 (2H, m), 3.94, 4.58 (2H, d, d, J = 9.3,9.3H
z), 3.54, 3.83 (3H, s, s), 3.25, 3.36 (2H, s, s), 2.
09, 2.11 (3H, s, s).

[0293]

Example 25 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N-phenoxyacetylhydrazone (Compound No. 1-33) Physical properties: solid Mass spectrum (EI) m / e: 430 (M ⁺ ) ^{, 383, 261. 1 H-NMR} (200MHz, CDCl 3) spectrum δ (ppm): 8.33, 9.9
7 (1H, s, s), 7.70-6.58 (11H, m), 4.57, 4.66 (2H, s,
s), 3.82, 3.92 (2H, s, s), 2.05, 2.22 (3H, m, m).

[0294]

Example 26 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-cyanomethylcarbonylhydrazone (Compound No. 1-37) Melting point: 133-134 ° C. Mass spectrum (EI) m / e: 363 ^{(M +), 316, 249.} 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.35 (1H ,
s), 7.57 (2H, d, J = 8.5Hz), 7.27 (2H, d, J = 8.5Hz), 6.
79 (1H, d, J = 3.7Hz), 6.61 (1H, d, J = 3.7Hz), 3.92 (2H,
s), 3.84 (2H, s), 2.11 (3H, s).

[0295]

Example 27 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N- (2-chloroethylcarbonyl) hydrazone (Compound No. 1-41) Physical properties: solid Mass spectrum (EI) m / e: 386 (M ⁺ ), 339, 293, 249. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.35 (1H,
s), 7.64 (2H, d, J = 8.5Hz), 7.35 (2H, d, J = 8.5Hz), 6.
86 (1H, d, J = 3.7Hz), 6.65 (1H, d, J = 3.7Hz), 3.98 (2H,
t, J = 6.8Hz), 3.93 (2H, s), 3.37 (2H, t, J = 6.8Hz),
1.65 (3H, s).

[0296]

Example 28 4-Chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N- (2-methylthioethylcarbonyl) hydrazone (Compound No. 1-4)
4) Physical properties: solid Mass spectrum (EI) m / e: 398 (M ⁺ ), 383, 351, 323, 24
^{9. 1 H-NMR (200MHz,} CDCl 3) spectrum δ (ppm): 8.31 (1H ,
s), 7.63 (2H, d, J = 8.4Hz), 7.35 (2H, d, J = 8.4Hz), 6.
86 (1H, d, J = 3.7Hz), 6.64 (1H, d, J = 3.7Hz), 3.94 (2H,
s), 3.19 (2H, t, J = 7.3Hz), 2.97 (2H, t, J = 7.3Hz),
2.30 (3H, s), 2.20 (3H, s).

[0297]

Example 29 4-Chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N- (4-chlorobenzoyl) hydrazone (Compound No. 1-46) Melting point: 190-191 ° C. Mass spectrum (EI) m / ^{e: 434 (M +),} 387, 354. 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 10.62 (1H ,
s), 7.49-7.75 (8H, m), 6.92 (1H, d, J = 3.7Hz), 6.65 (1
(H, d, J = 3.7Hz), 3.96 (2H, s), 2.06 (3H, s).

[0298]

Example 30 4-Chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N- (pyridincarb-2-yl) hydrazone (Compound No. 1-48) Melting point: 154-156 ° C. Mass spectrum (EI) ^{m / e: 401 (M +} ), 354, 295. 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 10.83 (1H ,
s), 8.38 (1H, dd, J = 0.9, 4.0Hz), 8.25 (1H, d, J = 7.8
Hz), 7.79-7.90 (1H, m), 7.34-7.66 (6H, m), 6.82 (1H, m
d, J = 3.7Hz), 6.73 (1H, d, J = 3.7Hz), 3.85 (2H, s), 2.
11 (3H, s).

[0299]

Example 31 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N- (pyridin-4-yl) hydrazone (Compound No. 1-50) Melting point: 157-158 ° C. Mass spectrum (EI) m / e: 401 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 10.84 (1H,
s), 8.71 (2H, d, J = 4.8Hz), 7.43-7.70 (6H, m), 6.92
(1H, s), 6.69 (1H, s), 3.96 (2H, s), 2.07 (3H, s).

[0300]

Example 32 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N- (thiophencarb-2-yl) hydrazone (Compound No.1-51) Physical properties: solid Mass spectrum (EI) m / e ^{: 405 (M +), 359} , 248. 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 7.90-8.11
(2H, s), 7.63 (1H, d, J = 8.4Hz), 7.46 (2H, d, J = 8.4H
z), 7.21 (1H, t, J = 4.0Hz), 6.91 (1H, d, J = 3.7Hz), 6.
63 (1H, d, J = 3.7Hz), 3.96 (2H, s), 2.06 (3H, s).

[0301]

Example 33 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-methoxycarbonylhydrazone (Compound No. 1-56) Physical property: solid Mass spectrum (EI) m / e: 354 (M ⁺ ) ^{. 1 H-NMR (200MHz,} CDCl 3) spectrum δ (ppm): 8.31, 7.6
2 (1H, brd.s, brd.s), 7.60-7.51 (2H, m), 7.33-7.25 (2
H, m), 7.06, 6.77 (1H, d, d, J = 3.6, 3.6Hz), 7.00,
6.57 (1H, d, d, J = 3.6, 3.6Hz), 3.92-3.83 (5H, m), 2.
16, 2.09 (3H, s, s).

[0302]

Example 34 4-chlorophenyl-5-methylsulfinylmethylthiophen-2-yl ketone = N-methoxycarbonylhydrazone (Compound No. 1-57) Physical properties: solid Mass spectrum (EI) m / e: 354 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.35, 7.6
9 (1H, brd.s, brd.s), 7.57-7.53 (2H, m), 7.33-7.24 (2
H, m), 7.20, 6.89 (1H, d, d, J = 3.6, 3.7Hz), 7.13,
6.66 (1H, d, d, J = 3.6, 3.7Hz), 4.29-4.08 (2H, m), 3.
84, 3.81 (3H, s, s), 2.59, 2.51 (3H, s, s).

[0303]

Example 35 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylhydrazone (Compound No. 1-58) Physical properties: solid Mass spectrum (EI) m / e: 368 (M ⁺ ) ^{, 321, 249. 1 H-NMR} (200MHz, CDCl 3) spectrum δ (ppm): 7.68, 8.2
9 (1H, s, s), 7.47-7.66 (2H, m), 7.22-7.35 (2H, m),
6.76, 7.06 (1H, d, d, J = 3.7, 3.7Hz), 6.57, 6.99 (1H,
d, d, J = 3.7, 3.7Hz), 4.19, 4.39 (2H, m, m), 3.83,
3.92 (2H, s, s), 2.09, 2.17 (3H, s, s), 1.04 (3H, m).

[0304]

Example 36 4-Chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-propoxycarbonylhydrazone (Compound No. 1-60) Physical properties: solid Mass spectrum (EI) m / e: 382 (M ⁺ ) ^{, 335, 266, 249. 1 H} -NMR (200MHz, CDCl 3) spectrum δ (ppm): 7.61, 8.2
8 (1H, s, s), 7.51-7.60 (2H, m), 7.27-7.34 (2H, m),
6.57, 7.03 (1H, d, d, J = 3.7, 3.7Hz), 6.76, 7.07 (1H,
d, d, J = 3.7, 3.7Hz), 4.11-4.26 (2H, m), 3.83, 3.93
(2H, s, s), 2.09, 2.17 (3H, s, s), 1.25-1.80 (4H, m),
0.98 (3H, t).

[0305]

Example 37 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N-butoxycarbonylhydrazone (Compound No. 1-62) Physical properties: solid Mass spectrum (EI) m / e: 396 (M ⁺ ) ^{, 349, 249. 1 H-NMR} (200MHz, CDCl 3) spectrum δ (ppm): 8.28 (1H ,
s), 7.50-7.64 (2H, m), 7.29-7.35 (2H, m), 6.76, 7.06
(1H, d, d, J = 3.7, 3.7Hz), 6.56, 7.00 (1H, d, d, J = 3.
7, 3.7Hz), 4.10, 4.29 (2H, s), 3.83, 3.93 (2H, s,
s), 2.09, 2.17 (3H, s, s), 1.21-1.78 (4H, m), 0.89-
1.03 (3H, m).

[0306]

Example 38 4-Chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N- (isobutoxycarbonyl) hydrazone (Compound No. 1-63) Physical properties: solid Mass spectrum (EI) m / e: 396 ( M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.22-7.63
(4H, m), 6.78, 7.06 (1H, d, d, J = 3.7, 3.7Hz), 6.57,
6.94 (1H, d, d, J = 3.7, 3.7Hz), 3.90-4.05 (2H, m), 3.
83, 3.92 (2H, s, s), 1.95-2.12 (4H, m), 0.90-1.03 (6
H, m).

[0307]

Example 39 4-Chlorophenyl 5-methylthiomethylthiophen-2-yl ketone N- (allyloxycarbonyl) hydrazone (Compound No. 1-65) Melting point: 119-120 ° C Mass spectrum (EI) m / e ^{: 380 (M +), 333} , 266, 248. 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 7.65 (1H ,
s), 7.56 (2H, d, J = 3.7Hz), 7.29 (2H, d, J = 8.5Hz), 6.
77 (1H, d, J = 3.7Hz), 6.58 (1H, d, J = 3.7Hz), 5.78-6.0
8 (1H, m), 5.23-5.45 (2H, m), 4.70 (2H, d, J = 5.5Hz),
3.84 (2H, s), 2.09 (3H, s).

[0308]

Example 40 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N- (2-chloroethoxycarbonyl) hydrazone (Compound No. 1-6)
8) Physical properties: solid mass spectrum (EI) m / e: 402 (M +), 366, 355, 319. 1 H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 7.69, 8.3
8 (1H, s, s), 7.51-7.62 (2H, m), 7.22-7.37 (2H, m),
7.22-7.37 (2H, m), 7.22-7.37 (2H, m), 6.77, 7.07 (1H, m
d, d, J = 3.7, 3.7Hz), 6.58, 7.03 (1H, d, d, J = 3.7,
3.7Hz), 3.83, 3.93 (2H, s, s), 3.69-3.78 (2H, m), 2.
09, 2.167 (3H, s, s).

[0309]

Example 41 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N- (2,2,2
- trichloroethoxycarbonyl) hydrazone (Compound No. 1-73) Physical properties: solid mass spectrum (EI) m / e: 472 (M +), 425, 322. 1 H-NMR (200MHz, CDCl 3) spectrum [delta] (ppm) ： 7.91 (1H,
s), 7.67 (2H, d, J = 8.5Hz), 7.40 (2H, d, J = 8.5Hz), 6.
87 (1H, d, J = 3.7Hz), 6.70 (1H, d, J = 3.7Hz), 4.93 (2H,
s), 3.92 (2H, s), 2.18 (3H, s).

[0310]

Example 42 4-chlorophenyl-5-methylthiomethylthiophen-2-yl ketone = N-methylaminocarbonylhydrazone (Compound No. 1-88) Melting point: 174-176 ° C. Mass spectrum (EI) m / e: 352 (M ⁺ ) or 353 (M ⁺ ), 306, 2
49. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.53 (2H,
d, J = 8.3Hz), 7.44 (1H, s), 7.26 (2H, d, J = 8.3Hz), 6.7
5 (1H, d, J = 3.7Hz), 6.49 (1H, d, J = 3.7Hz), 6.13 (1H,
d, J = 5.0Hz), 3.85 (2H, s), 2.93 (3H, d, J = 5.0Hz), 2.
11 (3H, s).

[0311]

Example 43 4-Chlorophenyl = 5-methylthiomethylthiophen-2-yl = ketone = N-chloromethoxycarbonylhydrazone (Compound No. 1-71) Physical properties: solid Mass spectrum (EI) m / e: 388 (M ^{+ ), 341, 322, 293. 1} H-NMR (200MHz, CDCl 3) spectrum δ (ppm): 8.17, 8.7
7 (1H, s, s), 7.49-7.63 (2H, m), 7.61-7.71 (2H, m),
7.35-7.44 (2H, m), 6.87, 7.18 (1H, d, d, J = 3.7,3.7H
z), 6.60, 7.11 (1H, d, d, J = 3.7, 3.7Hz), 5.91 (2H,
s), 3.92, 4.02 (2H, s, s), 2.18, 2.26 (3H, s, s).

[0312]

Example 44 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylmethylhydrazone (Compound No. 1-328) Physical properties: solid Mass spectrum (EI) m / e: 396 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.45 (2H,
d, J = 8.2Hz), 7.26 (2H, d, J = 8.2Hz), 7.03 (2H, m), 6.2
3 (1H, t, J = 3.7Hz), 4.18 (2H, m), 4.09 (2H, d, J = 5.7H
z), 3.95 (2H, s), 2.58 (2H, q, J = 7.7Hz), 1.28 (6H,
m).

[0313]

Example 45 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N- (tert-
Butoxycarbonyl) hydrazone (Compound No. 1-35)
2) Physical properties: solid Mass spectrum (EI) m / e: 410 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.06, 6.7
5 (1H, d, d, J = 3.8, 3.4Hz), 6.99, 6.53 (1H, d, d, J =
3.8, 3.4Hz), 3.98, 3.86 (2H, s, s), 2.60, 2.52 (2H,
q, q, J = 7.7, 7.7Hz), 1.69, 1.49 (9H, s, s), 1.29,
1.24 (3H, t, t, J = 7.7, 7.7Hz).

[0314]

Example 46 4-bromophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylhydrazone (Compound No. 1-1189) Physical properties: gum Mass spectrum (EI) m / e: 426 ( M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.28, 7.5
8 (1H, brd.s, brd.s), 7.72-7.15 (4H, m), 7.06, 6.77
(1H, d, d, J = 3.6, 3.6Hz), 6.99, 6.56 (1H, d, d, J =
3.6, 3.6Hz), 4.32-4.20 (2H, m), 3.96, 3.87 (2H, s,
s), 2,60, 2.53 (2H, q, q, J = 7.3,7.3Hz), 1.40-1.21 (6
H, m).

[0315]

Example 47 4-chlorophenyl-5-ethylsulfinylmethylthiophen-2-yl ketone = N-ethoxycarbonylhydrazone (Compound No. 1-1190) Physical properties: solid Mass spectrum (EI) m / e: 442 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.26-6.54
(7H, m), 4.36-4.21 (2H, m), 3.96, 3.87 (2H, s, s), 2.
66-2.48 (2H, m), 1.37-1.21 (6H, m).

[0316]

Example 48 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone hydrazone (Compound No. 1-145) Melting point: 148-149 ° C Mass spectrum (EI) m / e: 328 (M ⁺ ) ^{. 1 H-NMR (200MHz,} CDCl 3) spectrum δ (ppm): 7.53 (2H ,
d, J = 8.5Hz), 7.32 (2H, d, J = 8.5Hz), 6.99 (1H, d, J = 3.
7Hz), 6.53 (1H, d, J = 3.7), 5.43 (2H, brd.s), 4.39 (2H,
s), 2.87 (3H, s).

[0317]

Example 49 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-acetylhydrazone (Compound No. 1-146) (one geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 370 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.24 (1H,
brd.s), 7.55 (2H, d, J = 8.6Hz), 7.26 (2H, d, J = 8.6H
z), 7.02 (1H, d, J = 3.7Hz), 6.67 (1H, d, J = 3.7Hz), 4.
42 (2H, s), 2.90 (3H, s), 2.38 (3H, s). (Other geometric isomers) Physical property: Solid Mass spectrum (EI) m / e: 370 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.72 (1H,
brd.s), 7.53 (2H, d, J = 8.7Hz), 7.34 (2H, d, J = 8.7H
z), 7.32 (1H, d, J = 3.6Hz), 7.13 (1H, d, J = 3.6Hz), 4.
50 (2H, s), 2.96 (3H, s), 2.43 (3H, s).

[0318]

Example 50 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-propionylhydrazone (Compound No. 1-147) (one geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 384 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.22 (1H,
brd.s), 7.56 (2H, d, J = 8.6Hz), 7.26 (2H, d, J = 8.6H
z), 7.01 (1H, d, J = 3.7Hz), 6.66 (1H, d, J = 3.7Hz), 4.
42 (2H, s), 2.90 (3H, s), 2.79 (2H, q, J = 7.5Hz), 1.22
(3H, t, J = 7.5Hz). (Other geometric isomers) Physical property: Solid Mass spectrum (EI) m / e: 384 (M ⁺ ). ¹ H-NMR (200MHz, CDCl ₃ ) spectrum δ (ppm) ): 8.69 (1H,
brd.s), 7.53 (2H, d, J = 8.7Hz), 7.34 (2H, d, J = 8.7H
z), 7.32 (1H, d, J = 3.6Hz), 7.13 (1H, d, J = 3.6Hz), 4.
50 (2H, s), 2.96 (3H, s), 2.84 (2H, q, J = 7.4Hz), 1.25
(3H, t, J = 7.4Hz).

[0319]

Example 51 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-butyrylhydrazone (Compound No. 1-148) (one geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 398 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.22 (1H,
brd.s), 7.55 (2H, d, J = 8.4Hz), 7.26 (2H, d, J = 8.4H
z), 7.02 (1H, d, J = 3.9Hz), 6.66 (1H, d, J = 3.9Hz), 4.
42 (2H, s), 2.90 (3H, s), 2.74 (2H, t, J = 7.5Hz), 1.75
(2H, tq, J = 7.5, 7.5Hz), 1.03 (3H, t, J = 7.5Hz). (Other geometric isomers) Physical properties: Solid Mass spectrum (EI) m / e: 398 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.69 (1H,
brd.s), 7.53 (2H, d, J = 8.6Hz), 7.40-7.30 (3H, m), 7.
13 (1H, d, J = 3.5Hz), 4.50 (2H, s), 2.96 (3H, s), 2.80
(2H, t, J = 7.4Hz), 1.78 (2H, tq, J = 7.4, 7.4Hz), 1.05
(3H, t, J = 7.4Hz).

[0320]

Example 52 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-octanoylhydrazone (Compound No. 1-157) Physical properties: solid Mass spectrum (EI) m / e: 454 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.75, 8.3
4 (1H, brd.s, brd.s), 7.60-7.48 (2H, m), 7.38-7.00 (3
H, m), 7.12, 6.67 (1H, d, d, J = 3.6, 3.8Hz), 4.50,
4.42 (2H, s, s), 2.95, 2.90 (3H, s, s), 2.90-2.23 (2
H, m), 1.82-1.20 (10H, m), 0.95-0.80 (3H, m).

[0321]

Example 53 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-cyclopropylcarbonylhydrazone (Compound No. 1-16)
0) Physical properties: solid Mass spectrum (EI) m / e: 396 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.97, 8.6
5 (1H, brd.s, brd.s), 7.60-7.50 (2H, m), 7.38-7.00 (3
H, m), 7.15, 6.67 (1H, d, d, J = 3.6, 3.8Hz), 4.51,
4.42 (2H, s, s), 2.95, 2.89 (3H, s, s), 2.82-2.68 (1
H, m), 1.63-0.83 (4H, m).

[0322]

Example 54 4-chlorophenyl-5-methylsulfonylmethylthiophen-2-yl ketone = N-cyclopentylcarbonylhydrazone (Compound No. 1-16)
2) Physical properties: solid Mass spectrum (EI) m / e: 424 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.70, 8.2
6 (1H, brd.s, brd.s), 7.65-7.50 (2H, m), 7.38-7.00 (3
H, m), 7.15, 6.66 (1H, d, d, J = 3.7, 3.7Hz), 4.50,
4.42 (2H, s, s), 3.68-3.50 (1H, m), 2.95, 2.90 (3H,
s, s), 2.10-1.50 (8H, m).

[0323]

Example 55 4-chlorophenyl-5-methylsulfonylmethylthiophen-2-yl ketone = N-cyclohexylcarbonylhydrazone (Compound No. 1-16)
3) Physical properties: solid Mass spectrum (EI) m / e: 438 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.60, 8.1
4 (1H, brd.s, brd.s), 7.60-7.48 (2H, m), 7.38-7.00 (3
H, m), 7.15, 6.67 (1H, d, d, J = 3.7, 3.7Hz), 4.50,
4.43 (2H, s, s), 3.32-3.08 (1H, m), 2.95, 2.91 (3H,
s, s), 2.05-1.10 (10H, m).

[0324]

Example 56 4-chlorophenyl-5-methylsulfonylmethylthiophen-2-yl ketone = N-acryloylhydrazone (Compound No. 1-164) Physical properties: solid Mass spectrum (EI) m / e: 382 (M ⁺ ) . ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.81, 8.3
2 (1H, brd.s, brd.s), 7.60-7.50 (2H, m), 7.40-7.00 (4
H, m), 7.16, 6.68 (1H, d, d, J = 3.7, 3.8Hz), 6.65-6.
48 (1H, m), 6.00-5.85 (1H, m), 4.51, 4.43 (2H, s, s),
2.97, 2.90 (3H, s, s).

[0325]

Example 57 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-methoxyacetylhydrazone (Compound No. 1-174) Physical properties: solid Mass spectrum (EI) m / e: 400 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.26, 8.2
7 (1H, brd.s, brd.s), 7.58, 7.56 (2H, d, d, J = 8.5,
8.5Hz), 7.31, 7.25 (2H, d, d, J = 8.5, 8.5Hz), 7.07,
7.02 (1H, d, d, J = 3.8, 3.8Hz), 6.80, 6.68 (1H, d, d,
J = 3.8, 3.8Hz), 4.55, 4.43 (2H, s, s), 4.41, 3.96 (2
H, s, s), 3.53, 3.26 (3H, s, s), 2.90, 2.87 (3H, s,
s).

[0326]

Example 58 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (2-
Chloroethylcarbonyl) hydrazone (Compound No. 1-
184) Melting point: 131-134 ° C. Mass spectrum (EI) m / e: 382 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.37 (1H,
brd.s), 7.56 (2H, d, J = 8.5Hz), 7.26 (2H, d, J = 8.5H
z), 7.03 (1H, d, J = 3.8Hz), 6.69 (1H, d, J = 3.8Hz), 4.
43 (2H, s), 3.87 (2H, t, J = 6.7Hz), 3.26 (2H, t, J = 6.7
Hz), 2.90 (3H, s).

[0327]

Example 59 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-benzoylhydrazone (Compound No. 1-188) Melting point: 207-212 ° C Mass spectrum (EI) m / e: 432 ( M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.95-7.20
(9H, m), 7.07 (1H, br.d, J = 3.6Hz), 6.78 (1H, br.d, J
= 3.6Hz), 4.41 (2H, s), 2.88 (3H, s).

[0328]

Example 60 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (4-
Chlorobenzoyl) hydrazone (Compound No. 1-18)
9) Melting point: 190-192 ° C Mass spectrum (EI) m / e: 466 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.70-7.20
(8H, m), 7.06 (1H, br.d, J = 4.1Hz), 6.75 (1H, br.d, J
= 4.1Hz), 4.42 (2H, s), 2.89 (3H, s).

[0329]

Example 61 4-chlorophenyl-5-methylsulfonylmethylthiophen-2-yl ketone = N-methoxycarbonylhydrazone (Compound No. 1-199) (one geometric isomer) Melting point: 188-190 ° C. ¹ H- NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.71 (1H,
brd.s), 7.56 (2H, d, J = 8.4Hz), 7.27 (2H, d, J = 8.4H
z), 7.03 (1H, d, J = 3.7Hz), 6.69 (1H, d, J = 3.7Hz), 4.
40 (2H, s), 3.81 (3H, s), 2.87 (3H, s). (Other geometric isomers) Melting point: 158-160 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.24 (1H,
brd.s), 7.55 (2H, d, J = 8.6Hz), 7.35-7.29 (3H, m), 7.
15 (1H, d, J = 3.7Hz), 4.51 (2H, s), 3.86 (3H, s), 2.96
(3H, s).

[0330]

Example 62 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-ethoxycarbonylhydrazone (Compound No. 1-200) Physical properties: solid Mass spectrum (EI) m / e: 400 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.21, 7.6
7 (1H, brd.s, brd.s), 7.60-7.50 (2H, m), 7.38-7.00 (3
H, m), 7.16, 6.69 (1H, d, d, J = 3.8, 3,6Hz), 4.51,
4.40 (2H, s, s), 4.40-4.20 (2H, m), 2.97, 2.87 (3H,
s, s), 1.40-1.25 (3H, m).

[0331]

EXAMPLE 63 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (propoxycarbonyl) hydrazone (Compound No. 1-20)
1) Physical properties: solid Mass spectrum (EI) m / e: 414 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.21, 7.6
7 (1H, brd.s, brd.s), 7.60-7.50 (2H, m), 7.35-7.00 (3
H, m), 7.16, 6.69 (1H, d, d, J = 3.7, 3.7Hz), 4.51,
4.40 (2H, s, s), 4.25-4.10 (2H, m), 2.97, 2.87 (3H,
s, s), 1.80-1.60 (2H, m), 1.00-0.90 (3H, m).

[0332]

Example 64 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (isopropoxycarbonyl) hydrazone (Compound No. 1-2)
04) Physical properties: solid Mass spectrum (EI) m / e: 428 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.21, 7.6
7 (1H, brd.s, brd.s), 7.60-7.50 (2H, m), 7.35-7.00 (3
H, m), 7.16, 6.69 (1H, d, d, J = 3.6, 3.6Hz), 4.51,
4.40 (2H, s, s), 4.05-3.95 (2H, m), 2.96, 2.87 (3H,
s, s), 2.10-1.85 (1H, m), 1.00-0.90 (6H, m).

[0333]

Example 65 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N-allyloxycarbonylhydrazone (Compound No. 1-206) Physical properties: solid Mass spectrum (EI) m / e: 412 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.29, 7.7
3 (1H, brd.s, brd.s), 7.60-7.52 (2H, m), 7.35-7.00 (3
H, m), 7.15, 6.69 (1H, d, d, J = 3.6, 3.6Hz), 6.08-5.
83 (1H, m), 5.42-5.20 (2H, m), 4.78-4.65 (2H, m), 4.5
1, 4.40 (2H, s, s), 2.96, 2.87 (3H, s, s).

[0334]

Example 66 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (2-
(Methoxyethoxycarbonyl) hydrazone (Compound No. 1-207) (one geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 430 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ ( ppm): 7.81 (1H,
brd.s), 7.55 (2H, d, J = 8.6Hz), 7.26 (2H, d, J = 8.6H
z), 7.03 (1H, d, J = 3.8Hz), 6.68 (1H, d, J = 3.8Hz), 4.
40 (2H, s), 4.40-4.28 (2H, m), 3.68-3.55 (2H, m), 3.3
7 (3H, s), 2.86 (3H, s). (Other geometric isomers) Physical property: Solid Mass spectrum (EI) m / e: 430 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.36 (1H,
brd.s), 7.56 (2H, d, J = 8.7Hz), 7.35-7.25 (3H, m), 7.
14 (1H, d, J = 3.6Hz), 4.51 (2H, s), 4.43-4.35 (2H, m),
3.68-3.60 (2H, m), 3.39 (3H, s), 2.97 (3H, s).

[0335]

Example 67 4-chlorophenyl-5-methylsulfonylmethylthiophen-2-yl ketone = N- (2-
Chloroethoxycarbonyl) hydrazone (Compound No. 1)
-209) Physical properties: solid Mass spectrum (EI) m / e: 434 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.36, 7.7
9 (1H, brd.s, brd.s), 7.60-7.52 (2H, m), 7.35-7.00 (3
H, m), 7.17, 6.70 (1H, d, d, J = 3.6, 3.7Hz), 4.50-4.
38 (2H, m), 4.52, 4.41 (2H, s, s), 3.80-3.63 (2H, m),
2.97, 2.87 (3H, s, s).

[0336]

EXAMPLE 68 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (methylaminocarbonyl) hydrazone (Compound No. 1-22)
9) Physical properties: solid Mass spectrum (EI) m / e: 385 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.06-7.40
(3H, m), 7.40-6.97 (3H, m), 7.14, 6.61 (1H, d, d, J =
3.6, 3.8Hz), 6.28-6.08 (1H, m), 4.50, 4.42 (2H, s,
s), 3.00-2.75 (6H, m).

[0337]

Example 69 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (4-
(Chlorophenylaminocarbonyl) hydrazone (Compound No. 1-232) Physical properties: solid Mass spectrum (EI) m / e: 481 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.20-7.00
(11H, m), 7.22, 6.69 (1H, d, d, J = 3.6, 3.8Hz), 4.5
1, 4.45 (2H, s, s), 2.96, 2.92 (3H, s, s).

[0338]

Example 70 4-Chlorophenyl 5-methylsulfonylmethylthiophen-2-yl ketone N- (methylaminothiocarbonyl) hydrazone (Compound No. 1-)
233) (One geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 401 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.04, 8.4
8 (1H, brd.s, brd.s), 7.60-7.15 (4H, m), 7.09, 7.00
(1H, d, d, J = 4.1, 3.7Hz), 6.88, 6.69 (1H, d, d, J =
4.1, 3.7Hz), 4.51, 4.43 (2H, s, s), 3.27, 3.13 (3H,
d, d, J = 4.8, 5.1Hz), 2.96, 2.90 (3H, s, s). (Other geometric isomers) Physical property: Solid Mass spectrum (EI) m / e: 401 (M ⁺ ). ¹ H -NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.62-7.37
(4H, m), 7.19, 7.06 (1H, d, d, J = 4.0, 3.8Hz), 7.12,
6.86 (1H, d, d, J = 4.0, 3.8Hz), 6.05-5.95, 5.78-5.7
0 (1H, m, m), 4.49, 4.43 (2H, s, s), 3.25, 3.21 (3H,
d, d, J = 4.7, 4.8Hz), 2.91, 2.85 (3H, s, s).

[0339]

Example 71 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone hydrazone (Compound No. 1-288) Physical property: solid Mass spectrum (EI) m / e: 310 (M ⁺ ). ¹ H -NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.53-7.45
(2H, m), 7.35-7.27 (2H, m), 7.03, 6.73 (1H, d, d, J =
3.7, 3.7Hz), 6.99, 6.40 (1H, d, d, J = 3.7, 3.7Hz),
5.85, 5.31 (2H, brd.s, brd.s), 3.96, 3.86 (2H, s,
s), 2.58, 2.55 (2H, q, q, J = 7.4, 7.4Hz), 1.29, 1.25
(3H, t, t, J = 7.4, 7.4Hz).

[0340]

Example 72 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-acetylhydrazone (Compound No. 1-290) Physical property: solid Mass spectrum (EI) m / e: 352 (M ⁺ ) ^{. 1 H-NMR (200MHz,} CDCl 3) spectrum δ (ppm): 7.42-7.37
(2H, m), 7.23-7.16 (2H, m), 6.91-6.84 (2H, m), 3.91,
3.90 (2H, s, s), 2.58, 2.54 (2H, q, q, J = 7.1,7.1Hz),
2.30 (3H, s), 1.66-1.59 (3H, m).

[0341]

Example 73 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-propionylhydrazone (Compound No. 1-291) Melting point: 112-117 ° C Mass spectrum (EI) m / e: 366 ( M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.21 (1H,
brd.s), 7.56-7.51 (2H, m), 7.29-7.23 (2H, m), 6.78-6.
75 (1H, m), 6.54-6.52 (1H, m), 3.89, 3.86 (2H, s, s),
2.79 (2H, q, J = 7.3Hz), 2.55 (2H, q, J = 7.4Hz), 1.59-
1.11 (6H, m).

[0342]

Example 74 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-butyrylhydrazone (Compound No. 1-292) Melting point: 100-107 ° C. Mass spectrum (EI) m / e: 380 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.83-7.77
(2H, m), 7.50-7.45 (3H, m), 7.02 (1H, d, J = 3.8Hz), 3.
94 (2H, s), 2.57 (2H, q, J = 7.4Hz), 2.34 (2H, t, J = 7.3
Hz), 1.78-1.54 (2H, m), 1.27 (3H, t, J = 7.4Hz), 0.98
(3H, t, J = 7.4Hz).

[0343]

Example 75 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-isobutyrylhydrazone (Compound No. 1-293) Melting point: 112-117 ° C Mass spectrum (EI) m / e: 380 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.25 (1H,
brd.s), 7.57-7.50 (2H, m), 7.29-7.24 (2H, m), 6.77 (1
H, d, J = 3.7Hz), 6.53 (1H, d, J = 3.7Hz), 3.89 (2H, s),
3.58-3.92 (1H, m), 2.55 (2H, q, J = 7.5Hz), 1.31-1.14
(9H, m).

[0344]

Example 76 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-valerylhydrazone (Compound No. 1-294) Physical property: solid Mass spectrum (EI) m / e: 394 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.63-6.52
(7H, m), 3.94, 3.89 (2H, s, s), 2.63-2.50 (2H, m),
2.39-2.28 (2H, m), 1.71-1.50 (3H, m), 1.47-1.20 (2H, m
m), 1.02-0.86 (5H, m).

[0345]

Example 77 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-decanoylhydrazone (Compound No. 1-303) Melting point: 134-143 ° C Mass spectrum (EI) m / e: 464 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.82, 7.7
8 (1H, brd.s, brd.s), 7.52-7.44 (2H, m), 7.30-7.20 (3
H, m), 7.03-7.01 (1H, m), 3.94 (2H, s), 2.57 (2H, q,
J = 7.3Hz), 2.35 (2H, t, J = 7.3Hz), 1.67-1.55 (5H, m),
0.91-0.84 (15H, m).

[0346]

Example 78 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-cyclopropylcarbonylhydrazone (Compound No. 1-304) Melting point: 120-125 ° C. Mass spectrum (EI) m / e: 317 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.82-7.77
(2H, m), 7.50-7.44 (4H, m), 7.03-7.00 (1H, m), 3.94 (2
H, s), 2.57 (2H, q, J = 7.4Hz), 1.67-1.53 (1H, m), 1.27
(3H, t, J = 7.4Hz), 1.11-0.87 (4H, m).

[0347]

Example 79 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-cyclopentylcarbonylhydrazone (Compound No. 1-306) Physical property: solid Mass spectrum (EI) m / e: 406 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.76 (1H,
brd.s), 7.55-7.48 (2H, m), 7.30-7.23 (2H, m), 6.77 (1
H, d, J = 3.7Hz), 6.53 (1H, d, J = 3.7Hz), 3.89 (2H, s),
3.70-3.51 (1H, m), 2.55 (2H, q, J = 7.5Hz), 2.05-1.48
(8H, m), 1.27 (3H, t, J = 7.4Hz).

[0348]

Example 80 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-cyclohexylcarbonylhydrazone (Compound No. 1-307) (one geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 420 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.16 (1H,
brd.s), 7.56-7.49 (2H, m), 7.28-7.23 (2H, m), 6.77 (1
H, d, J = 3.7Hz), 6.54 (1H, d, J = 3.8Hz), 3.90 (2H, s),
3.34-3.11 (1H, m), 2.56 (2H, q, J = 7.4Hz), 1.67-1.20
(13H, m). (Other geometric isomers) Physical properties: solid Mass spectrum (EI) m / e: 420 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.75 (1H) ,
brd.s), 7.57-7.51 (2H, m), 7.36-7.31 (2H, m), 7.04 (1
H, d, J = 3.6Hz), 6.97 (1H, d, J = 3.5Hz), 3.95 (2H, s),
3.40-3.22 (1H, m), 2.59 (2H, q, J = 7.3Hz), 1.98-1.18
(13H, m).

[0349]

Example 81 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-acryloylhydrazone (Compound No. 1-308) Physical properties: solid Mass spectrum (EI) m / e: 364 (M ⁺ ) . ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.52-7.28
(2H, m), 7.19-6.95 (2H, m), 6.93-6.83 (2H, m), 6.49-
6.40 (1H, m), 5.80-5.73 (2H, m), 3.92, 3.89 (2H, s,
s), 2.64-2.47 (2H, m), 1.33-1.19 (3H, m).

[0350]

Example 82 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-methacryloylhydrazone (Compound No. 1-309) Physical properties: oil Mass spectrum (EI) m / e: 378 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.53, 7.5
9 (1H, brd.s, brd.s), 7.58-7.53 (2H, m), 7.34-7.28 (2
H, m), 7.09-6.61 (2H, m), 6.22-5.29 (2H, m), 3.98,
3.87 (2H, s, s), 2.61-2.48 (2H, m), 2.05-1.87 (3H,
m), 1.33-1.20 (3H, m).

[0351]

Example 83 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-allyloxycarbonylhydrazone (Compound No. 1-314) Melting point: 113-114 ° C. Mass spectrum (EI) m / e: 378 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.19 (1H,
brd.s), 7.56-7.51 (2H, m), 7.28-7.23 (2H, m), 6.78 (1
H, d, J = 3.5Hz), 6.55 (1H, d, J = 3.6Hz), 6.18-5.94 (1
H, m), 5.34-5.20 (2H, m), 3.90 (2H, s), 3.57 (2H, d,
J = 6.6Hz), 2.56 (2H, q, J = 7.0Hz), 1.31-1.23 (3H, m).

[0352]

Example 84 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-methoxyacetylhydrazone (Compound No. 1-319) Physical properties: solid Mass spectrum (EI) m / e: 382 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.18, 8.2
4 (1H, brd.s, brd.s), 7.59-7.52 (2H, m), 7.33-7.22 (2
H, m), 6.79-6.54 (2H, m), 3.98, 3.96 (2H, s, s), 3.5
4, 3.25 (3H, s, s), 3.54, 3.25 (3H, s, s), 2.61-2.49
(2H, m), 1.33-1.21 (3H, m).

[0353]

Example 85 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-phenoxyacetylhydrazone (Compound No. 1-321) Physical properties: solid Mass spectrum (EI) m / e: 444 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.83-7.77
(2H, m), 7.50-7.45 (3H, m), 7.35-7.28 (2H, m), 7.03-
6.89 (4H, m), 4.62 (2H, s), 3.95 (2H, s), 2.57 (2H, q,
J = 7.4Hz), 1.34-1.23 (3H, m).

[0354]

Example 86 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-benzoylhydrazone (Compound No. 1-333) Physical properties: solid Mass spectrum (EI) m / e: 414 (M ⁺ ) . ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.04-7.98
(2H, m), 7.92-7.87 (2H, m), 7.68-7.58 (3H, m), 7.53-
7.35 (2H, m), 7.13 (1H, d, J = 3.7Hz), 6.87 (1H, d, J = 3.
7Hz), 3.89 (2H, s), 2.54 (2H, q, J = 7.4Hz), 1.24 (3H,
t, J = 7.3Hz).

[0355]

Example 87 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (4-chlorobenzoyl) hydrazone (Compound No. 1-334) Physical properties: solid Mass spectrum (EI) m / e: 448 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.98-7.80
(4H, m), 7.62-7.36 (4H, m), 7.09 (1H, d, J = 3.6Hz), 6.
87 (1H, d, J = 3.7Hz), 3.89 (2H, s), 2.54 (2H, q, J = 7.4
Hz), 1.29-1.20 (3H, m).

[0356]

Example 88 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N- (pyridincarb-2-yl) hydrazone (Compound No. 1-336) Melting point: 120-130 ° C. Mass spectrum (EI) ) m / e: 415 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 11.46, 1
0.83 (1H, brd.s, brd.s), 8.38-8.21 (2H, m), 7.88-7.56
(3H, m), 7.45-7.32 (3H, m), 7.16-6.71 (2H, m), 4.01,
3.89 (2H, s, s), 2.65-2.50 (2H, m), 1.71-1.21 (3H,
m).

[0357]

Example 89 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (thiophencarb-2-yl) hydrazone (Compound No. 1-33)
9) Melting point: 120-125 ° C Mass spectrum (EI) m / e: 420 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.00-7.09
(9H, m), 6.87 (1H, d, J = 3.7Hz), 3.88 (2H, s), 2.53 (2
H, q, J = 7.4Hz), 1.24 (3H, t, J = 7.3Hz).

[0358]

Example 90 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylhydrazone (Compound No. 1-346) Physical property: solid Mass spectrum (EI) m / e: 382 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.29, 7.6
0 (1H, brd.s, brd.s), 7.57-7.51 (2H, m), 7.33-7.25 (2
H, m), 7.06, 6.77 (1H, d, d, J = 3.5, 3.7Hz), 7.00,
6.56 (1H, d, d, J = 3.6, 3.7Hz), 4.37-4.19 (2H, m), 3.
97, 3.87 (2H, s, s), 2.68-2.48 (2H, m), 1.37-1.20 (3
H, m).

[0359]

Example 91 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-propoxycarbonylhydrazone (Compound No. 1-348) Physical property: solid Mass spectrum (EI) m / e: 396 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.28, 7.6
0 (1H, brd.s, brd.s), 7.60-7.51 (2H, m), 7.33-7.25 (2
H, m), 7.06, 6.77 (1H, d, d, J = 3.7, 3.7Hz), 7.00,
6.56 (1H, d, d, J = 3.6, 3.7Hz), 4.24-4.11 (2H, m), 3.
97, 3.87 (2H, s, s), 2.68-2.47 (2H, m), 1.80-1.65 (2
H, m), 1.33-1.20 (3H, m), 1.01-0.91 (3H, m).

[0360]

Example 92 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-isobutoxycarbonylhydrazone (Compound No. 1-351) Physical properties: solid Mass spectrum (EI) m / e: 410 (M) ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.24, 7.6
0 (1H, brd.s, brd.s), 7.58-7.52 (2H, m), 7.34-7.29 (2
H, m), 7.06, 6.77 (1H, d, d, J = 3.7, 3.7Hz), 7.00,
6.56 (1H, d, d, J = 3.5, 3.7Hz), 4.05-3.87 (4H, m), 2.
67-2.48 (2H, m), 2.10-1.91 (1H, m), 1.34-1.21 (3H, m
m), 0.99-0.93 (6H, m).

[0361]

Example 93 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-allyloxycarbonylhydrazone (Compound No. 1-353) Physical properties: solid Mass spectrum (EI) m / e: 394 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.61-7.51
(2H, m), 7.35-7.23 (2H, m), 7.06, 6.77 (1H, d, d, J =
3.4, 3.7Hz), 7.00, 6.57 (1H, d, d, J = 3.5, 3.7Hz),
6.10-5.86 (1H, m), 5.42-5.23 (2H, m), 4.75-4.65 (2H, m
m), 3.96, 3.87 (2H, s, s), 2.66-2.47 (2H, m), 1.35-
1.21 (3H, m).

[0362]

Example 94 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (2-methoxyethoxycarbonyl) hydrazone (Compound No. 1-3)
54) Melting point: 110-114 ° C Mass spectrum (EI) m / e: 412 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.76 (1H,
brd.s), 7.76-7.51 (2H, m), 7.29-7.24 (2H, m), 6.76 (1
H, d, J = 4.0Hz), 6.56 (1H, d, J = 3.7Hz), 4.40-3.32 (2
H, m), 3.87 (2H, s), 3.82-3.59 (2H, m), 3.39 (3H, s),
2.53 (2H, q, J = 7.5Hz), 1.25 (3H, t, J = 7.4Hz).

[0363]

Example 95 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (2-chloroethoxycarbonyl) hydrazone (Compound No. 1-35)
6) Physical properties: solid Mass spectrum (EI) m / e: 416 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.47, 7.7
0 (1H, brd.s, brd.s), 7.69-7.52 (2H, m), 7.35-7.25 (2
H, m), 7.07, 6.77 (1H, d, d, J = 3.7, 3.7Hz), 7.01,
6.58 (1H, d, d, J = 3.6, 3.7Hz), 4.52-4.38 (2H, m), 3.
97, 3.87 (2H, s, s), 3.78-3.67 (2H, m), 2.67-2.48 (2
H, m), 1.34-1.21 (3H, m).

[0364]

EXAMPLE 96 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (1-chloroethoxycarbonyl) hydrazone (Compound No. 1-36)
0) Melting point: 120-125 ° C Mass spectrum (EI) m / e: 420 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.83-7.76
(2H, m), 7.51-7.43 (3H, m), 7.03-7.00 (1H, m), 6.44 (1
H, q, J = 5.8Hz), 3.94 (2H, s), 2.57, 2.52 (2H, q, q, J
= 7.5, 7.3Hz), 1.83, 1.82 (3H, d, d, J = 5.8, 5.8Hz),
1.38-1.22 (3H, m).

[0365]

Example 97 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxyosalylhydrazone (Compound No. 1-373) Physical properties: solid Mass spectrum (EI) m / e: 410 (M) ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.70 (1H,
brd.s), 7.70-7.56 (2H, m), 7.38-6.73 (4H, m), 4.42-4.
25 (2H, m), 3.99, 3.88 (2H, s, s), 2.68-2.47 (2H, m),
1.40-1.21 (6H, m).

[0366]

Example 98 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-methylaminocarbonylhydrazone (Compound No. 1-376) Physical property: solid Mass spectrum (EI) m / e: 367 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.10, 7.5
5 (1H, brd.s, brd.s), 7.54-7.47 (2H, m), 7.29-7.23 (2
H, m), 7.04, 6.75 (1H, d, d, J = 3.7, 3.7Hz), 7.00,
6.49 (1H, d, d, J = 3.7, 3.7Hz), 6.27 (1H, brd.s), 3.9
5, 3.89 (2H, s, s), 3.37 (3H, s), 2.65-2.48 (2H, m),
1.33-1.23 (3H, m).

[0367]

Example 99 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (4-chlorophenylaminocarbonyl) hydrazone (Compound No. 1)
-379) Physical properties: solid Mass spectrum (EI) m / e: 463 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.23, 8.1
9 (1H, brd.s, brd.s), 7.59-7.48 (2H, m), 7.40-6.54 (6
H, m), 3.97, 3.91 (2H, s, s), 2.68-2.51 (2H, m), 1.3
4-1.22 (3H, m).

[0368]

Example 100 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-methanesulfonylhydrazone (Compound No. 1-384) Physical properties: oil Mass spectrum (EI) m / e: 388 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.58-7.45
(4H, m), 7.13-6.87 (2H, m), 3.94, 3.91 (2H, s, s), 3.
08 (3H, s), 2.62-2.51 (2H, m), 1.32-1.23 (3H, m).

[0369]

Example 101 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxymethyl-N-methoxycarbonylhydrazone (Compound No. 1-400) Physical property: oil Mass spectrum (EI) m / e: 426 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.40 (2H,
d, J = 8.9Hz), 7.34 (2H, d, J = 8.9Hz), 6.85 (1H, d, J = 3.
8Hz), 6.78 (1H, d, J = 3.8Hz), 5.00 (2H, s), 3.89 (2H,
s), 3.56 (3H, s), 3.44 (2H, q, J = 7.0Hz), 2.55 (2H, q,
J = 7.4Hz), 1.27 (3H, t, J = 7.4Hz), 1.17 (3H, t, J = 7.0
Hz).

[0370]

Example 102 4-Chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-methoxycarbonyl-N-methylthiomethylhydrazone (Compound No. 1-401) Physical properties: oil Mass spec (EI) m / e: 429 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.44 (2H,
d, J = 9.0Hz), 7.38 (2H, d, J = 9.0Hz), 6.85 (1H, d, J = 3.
7Hz), 6.78 (1H, d, J = 3.7Hz), 4.70 (2H, s), 3.89 (2H,
s), 3.55 (3H, s), 2.57 (2H, q, J = 7.4Hz), 2.15 (3H,
s), 1.27 (3H, t, J = 7.4Hz).

[0371]

Example 103 4-Chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-ethoxycarbonylmethyl-N-methoxycarbonylhydrazone (Compound No. 1-403) Physical properties: oil Mass spectrum (EI) m / e: 455 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.50 (2H,
d, J = 8.7Hz), 7.40 (2H, d, J = 8.7Hz), 6.83 (1H, d, J = 3.
7Hz), 6.78 (1H, d, J = 3.7Hz), 4.30 (2H, s), 4.22 (2H,
q, J = 7.1Hz), 3.87 (2H, s), 3.51 (3H, s), 2.55 (2H, q,
J = 7.4Hz), 1.29 (3H, t, J = 7.1Hz), 1.26 (3H, t, J = 7.4
Hz).

[0372]

Example 104 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-cyanomethyl-N-methoxycarbonylhydrazone (Compound No. 1)
-404) Physical properties: oil Mass spectrum (EI) m / e: 407 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.44 (2H,
d, J = 8.7Hz), 7.35 (2H, d, J = 8.7Hz), 6.88 (1H, d, J = 3.
8Hz), 6.83 (1H, d, J = 3.8Hz), 4.50 (2H, s), 3.90 (2H,
s), 3.60 (3H, s), 2.57 (2H, q, J = 7.4Hz), 1.27 (3H, t,
J = 7.4Hz).

[0373]

Example 105 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N- (methoxycarbonyl) -N-propionylhydrazone (Compound No. 1-409) Physical properties: Oil Mass spectrum (EI) m / e: 424 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.38 (2H,
d, J = 8.6Hz), 7.18 (2H, d, J = 8.6Hz), 6.88 (1H, d, J = 3.
8Hz), 6.83 (1H, d, J = 3.8Hz), 3.92 (2H, s), 3.77 (3H,
s), 2.69 (2H, q, J = 7.3Hz), 2.57 (2H, q, J = 7.3Hz), 1.
27 (3H, t, J = 7.3Hz), 0.97 (3H, t, J = 7.3Hz).

[0374]

Working Example 106 4-Chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone hydrazone (Compound No. 1-437) (one geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 342 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.45 (2H,
d, J = 8.7Hz), 7.32-7.26 (3H, m), 7.13 (1H, d, J = 3.7H
z), 5.86 (2H, brd.s), 4.46 (2H, s), 3.03 (2H, q, J = 7.4
(Hz), 1.44 (3H, t, J = 7.4Hz). (Other geometric isomers) Physical property: Solid Mass spectrum (EI) m / e: 342 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) Spectrum δ (ppm): 7.52 (2H,
d, J = 8.5Hz), 7.32 (2H, d, J = 8.5Hz), 6.98 (1H, d, J = 3.
8Hz), 6.52 (1H, d, J = 3.8Hz), 5.42 (2H, brd.s), 4.36
(2H, s), 2.98 (2H, q, J = 7.4Hz), 1.39 (3H, t, J = 7.4H
z).

[0375]

Example 107 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-acetylhydrazone (Compound No. 1-438) Physical properties: solid Mass spectrum (EI) m / e: 384 (M ⁺ ) ^{. 1 H-NMR (200MHz,} CDCl 3) spectrum δ (ppm): 8.23 (1H ,
s), 7.57 (2H, d, J = 8.4Hz), 7.26 (2H, d, J = 8.5Hz), 7.
01 (1H, d, J = 3.7Hz), 6.66 (1H, d, J = 3.7Hz), 4.39 (2H,
s), 3.00 (2H, q, J = 7.6Hz), 2.38 (3H, s), 1.42 (3H,
t, J = 7.5Hz).

[0376]

Working Example 108 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-propionylhydrazone (Compound No. 1-439) Physical properties: solid Mass spectrum (EI) m / e: 398 (M ⁺ ) ^{. 1 H-NMR (200MHz,} CDCl 3) spectrum δ (ppm): 8.22 (1H ,
s), 7.55 (2H, d, J = 8.5Hz), 7.26 (2H, d, J = 8.4Hz), 7.
00 (1H, d, J = 3.7Hz), 6.65 (1H, d, J = 3.8Hz), 4.39 (2H,
s), 3.00 (2H, q, J = 7.5Hz), 2.79 (2H, q, J = 7.5Hz),
1.42 (3H, t, J = 7.5Hz), 1.22 (3H, t, J = 7.5Hz).

[0377]

Example 109 4-chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N-butyrylhydrazone (Compound No. 1-440) Physical property: solid Mass spectrum (EI) m / e: 412 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.22 (1H,
s), 7.57-7.51 (2H, m), 7.31-7.23 (2H, m), 7.01 (1H, d,
J = 3.7Hz), 6.65 (1H, d, J = 3.7Hz), 4.39 (2H, s), 3.00
(2H, q, J = 7.6Hz), 2.74 (2H, t, J = 7.3Hz), 1.81-1.65
(2H, m), 1.43 (3H, t, J = 7.4Hz), 1.03 (3H, t, J = 7.3H
z).

[0378]

Example 110 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-
(3,3-Dimethylbutyryl) hydrazone (Compound No. 1-447) Physical properties: solid Mass spectrum (EI) m / e: 440 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm) ： 8.25 (1H,
s), 7.55 (2H, d, J = 8.4Hz), 7.25 (2H, d, J = 8.2Hz), 7.
02 (1H, d, J = 3.8Hz), 6.65 (1H, d, J = 3.9Hz), 4.40 (2H,
s), 3.01 (2H, q, J = 7.6Hz), 2.71 (2H, s), 1.43 (3H,
t, J = 7.5Hz), 1.11 (9H, s).

[0379]

Example 111 4-Chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N-octanoylhydrazone (Compound No. 1-449) Melting point: 114-117 ° C. Mass spectrum (EI) m / e: 468 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.21 (1H,
s), 7.55 (2H, dd, J = 6.6, 1.9Hz), 7.28-7.24 (2H, m),
7.01 (1H, d, J = 3.8Hz), 6.66 (1H, d, J = 3.8Hz), 4.39 (2
H, s), 2.98 (2H, q, J = 7.4Hz), 2.75 (2H, t, J = 7.3Hz),
1.80-1.60 (2H, m), 1.42 (3H, t, J = 7.4Hz), 1.50-1.22
(10H, m), 0.95-0.84 (3H, m).

[0380]

Example 112 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-cyclopropylcarbonylhydrazone (Compound No. 1-45)
2) Physical properties: solid Mass spectrum (EI) m / e: 410 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.34 (1H,
s), 7.58-7.54 (2H, m), 7.30-7.26 (2H, m), 7.00 (1H, d,
J = 3.7Hz), 6.66 (1H, d, J = 3.8Hz), 4.39 (2H, s), 3.05
-2.94 (2H, m), 2.80-2.66 (1H, m), 1.42 (3H, t, J = 7.5H
z), 1.20-0.95 (4H, m).

[0381]

Example 113 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-cyclobutylcarbonylhydrazone (Compound No. 1-45)
3) Melting point: 190-193 ° C Mass spectrum (EI) m / e: 424 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.14 (1H,
s), 7.57-7.53 (2H, m), 7.26-7.23 (2H, m), 7.00 (1H, d,
J = 3.7Hz), 6.64 (1H, d, J = 3.8Hz), 4.40 (2H, s), 3.91
-3.82 (1H, m), 3.01 (2H, q, J = 7.5Hz), 2.42-1.80 (6H,
m), 1.43 (3H, t, J = 7.5Hz).

[0382]

Example 114 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-cyclohexylcarbonylhydrazone (Compound No. 1-45)
5) Physical properties: solid Mass spectrum (EI) m / e: 452 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.14 (1H,
s), 7.55 (2H, d, J = 8.5Hz), 7.26 (2H, d, J = 8.4Hz), 7.
01 (1H, d, J = 3.8Hz), 6.66 (1H, d, J = 3.8Hz), 4.40 (2H,
s), 3.30-3.10 (1H, m), 3.01 (2H, q, J = 7.3Hz), 2.00-
1.18 (10H, m), 1.43 (34H, t, J = 7.3Hz).

[0383]

Example 115 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-cinnamoylhydrazone (Compound No. 1-457) Physical properties: solid Mass spectrum (EI) m / e: 472 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.86 (1H,
s), 7.90-7.26 (12H, m), 7.04 (1H, d, J = 3.8Hz), 6.71 (1
H, d, J = 3.8Hz), 6.43 (1H, d, J = 16.0Hz), 4.44 (2H,
s), 3.03 (2H, q, J = 7.5Hz), 1.44 (3H, t, J = 7.4Hz).

[0384]

Example 116 4-chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N-methoxyacetylhydrazone (Compound No. 1-466) Physical properties: solid Mass spectrum (EI) m / e: 414 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.26, 8.2
6 (1H, s, s), 7.68-6.67 (6H, m), 4.40, 4.38 (2H, s,
s), 4.05, 3.97 (2H, s, s), 3.35, 3.26 (3H, s, s), 3.
07-2.96 (2H, m), 1.50-1.37 (3H, m).

[0385]

Working Example 117 4-Chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N-phenoxyacetylhydrazone (Compound No. 1-468) Physical properties: solid Mass spectrum (EI) m / e: 476 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.88-6.59
(12H, m), 5.21-4.58 (2H, m), 4.48-4.38 (2H, m), 3.09
-2.92 (2H, m), 1.47-1.37 (3H, m).

[0386]

Example 118 4-chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N- (2
-Chloropropionyl) hydrazone (Compound No. 1-4)
76) Melting point: 145-147 ° C Mass spectrum (EI) m / e: 432 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.92 (1H,
brd.s), 7.58-7.53 (2H, m), 7.30-7.23 (2H, m), 7.02 (1
H, d, J = 3.8Hz), 6.68 (1H, d, J = 3.8Hz), 4.40 (2H, s),
3.88 (2H, t, J = 6.8Hz), 3.28 (2H, t, J = 6.7Hz), 3.01
(2H, q, J = 7.5Hz), 1.43 (3H, t, J = 7.4Hz).

[0387]

Example 119 4-Chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N- (2
-Methylthiopropionyl) hydrazone (Compound No. 1)
-479) Melting point: 139-141 ° C Mass spectrum (EI) m / e: 444 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.32 (1H,
s) 7.56 (2H, dd, J = 6.6,2.0Hz), 7.29-7.24 (2H, m), 7.
02 (1H, d, J = 3.7Hz), 6.67 (1H, d, J = 2.0Hz), 4.39 (2H,
s), 3.12-2.84 (6H, m), 2.20 (3H, s), 1.43 (3H, t, J =
7.5Hz).

[0388]

Example 120 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N- (4
-Chlorobenzoyl) hydrazone (Compound No. 1-48)
1) Melting point: 157-159 ° C Mass spectrum (EI) m / e: 480 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.64-7.30
(8H, m), 7.50 (1H, brd.s), 6.74 (1H, brd.s), 4.39 (2
H, s), 3.00 (2H, q, J = 7.6Hz), 1.42 (3H, t, J = 7.4Hz).

[0389]

Example 121 4-Chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl = ketone = N- (pyridincarb-3-yl) hydrazone (Compound No. 1-)
484) Melting point: 164-166 ° C Mass spectrum (EI) m / e: 447 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 10.89 (1H,
brd.s), 9.10-6.70 (8H, m), 4.81 (2H, s), 3.11 (2H, q,
J = 7.3Hz), 1.26 (3H, t, J = 7.3Hz).

[0390]

Example 122 4-Chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone N- (thiophencarb-2-yl) hydrazone (Compound No. 1)
-486) Melting point: 189-191 ° C Mass spectrum (EI) m / e: 452 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.50 (1H,
brd.s), 8.21 (1H, brd.s), 7.74 (1H, brd.s), 7.56 (2H,
d, J = 8.5Hz), 7.34 (2H, d, J = 8.5Hz), 7.22-7.15 (1H,
m), 7.06 (1H, d, J = 3.8Hz), 6.76 (1H, d, J = 3.8Hz), 4.
44 (2H, s), 3.02 (2H, q, J = 7.5Hz), 1.43 (3H, t, J = 7.5H
z).

[0391]

Example 123 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-methoxycarbonylhydrazone (Compound No. 1-491) (one geometric isomer) Physical property: solid Mass spectrum (EI) m / e: 400 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.60, 8.3
0 (1H, s), 7.52-7.56 (2H, m), 7.24-7.34 (2H, m), 7.04
(1H, d, J = 4.1Hz), 6.68 (1H, d, J = 4.1Hz), 4.37 (2H,
s), 3.82 (3H, s), 2.91 (2H, q, J = 7.5Hz), 1.40 (3H, t,
(Other geometric isomers) Physical properties: solid Mass spectrum (EI) m / e: 400 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.27 (1H) ,
s), 7.57 (2H, d, J = 6.7Hz), 7.34 (2H, d, J = 6.7Hz), 7.
33 (1H, d, J = 4.1Hz), 7.16 (1H, d, J = 4.1Hz), 4.49 (2H,
s), 3.88 (3H, s), 3.33 (2H, q, J = 7.5Hz), 1.48 (3H,
t, J = 7.6Hz).

[0392]

Example 124 4-chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N-propoxycarbonylhydrazone (Compound No. 1-493) Physical properties: solid Mass spectrum (EI) m / e: 428 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.23, 7.6
6 (1H, s, s), 7.60-6.66 (6H, m), 4.47, 4.37 (2H, s,
s), 4.24-4.13 (2H, m), 3.12-2.92 (2H, m), 1.80-1.60
(2H, m), 1.50-1.35 (3H, m), 1.01-0.90 (3H, m).

[0393]

Example 125 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-butoxycarbonylhydrazone (Compound No. 1-495) Physical property: solid Mass spectrum (EI) m / e: 442 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.23, 7.6
6 (1H, s, s), 7.59-6.66 (6H, m), 4.47, 4.37 (2H, s,
s), 4.30-4.17 (2H, m), 3.12-2.92 (2H, s), 1.72-1.52
(2H, m), 1.50-1.36 (5H, m), 0.99-0.90 (3H, m).

[0394]

Working Example 126 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-isobutoxycarbonylhydrazone (Compound No. 1-49)
6) Physical properties: solid Mass spectrum (EI) m / e: 442 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.25, 7.6
9 (1H, s, s), 7.58-6.65 (6H, m), 4.48, 4.37 (2H, s,
s), 4.03-3.95 (2H, m), 3.12-2.91 (2H, m), 2.04-1.94
(1H, m), 1.70-1.39 (3H, m), 0.98-0.92 (6H, m).

[0395]

Example 127 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-allyloxycarbonylhydrazone (Compound No. 1-49)
8) Physical properties: solid Mass spectrum (EI) m / e: 426 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.29, 7.7
2 (1H, s, s), 7.59-6.66 (6H, m), 6.05-5.83 (1H, m),
5.40-5.23 (2H, m), 4.74-4.67 (2H, m), 4.47, 4.37 (2H, m
s, s), 3.11-2.91 (2H, m), 1.48-1.35 (3H, m).

[0396]

Example 128 4-Chlorophenyl = 5-ethylsulfonylmethylthiophen-2-yl = ketone = N- (2
-Methoxyethoxycarbonyl) hydrazone (Compound No. 1-499) Physical property: solid Mass spectrum (EI) m / e: 444 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.80 (1H) ,
brd.s), 7.56 (2H, d, J = 8.5Hz), 7.27 (2H, d, J = 8.5H
z), 7.03 (1H, d, J = 4.0Hz), 6.68 (1H, d, J = 4.0Hz), 4.
37 (2H, s), 4.37-4.33 (2H, m), 3.64-3.59 (2H, m), 3.3
8 (3H, s), 2.97 (2H, q, J = 7.6Hz), 1.40 (3H, t, J = 7.6H
z).

[0397]

Working Example 129 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N- (2
-Chloroethoxycarbonyl) hydrazone (Compound No. 1-501) Physical property: solid Mass spectrum (EI) m / e: 448 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.39, 7.7
9 (1H, s, s), 7.59-6.67 (6H, m), 4.48-4.37 (4H, m),
3.74-3.68 (2H, m), 3.11-2.92 (2H, m), 1.49-1.35 (3H,
m).

[0398]

Example 130 4-Chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N-ethoxyoxalylhydrazone (Compound No. 1-518) Physical properties: solid Mass spectrum (EI) m / e: 442 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.76 (1H,
s), 7.61 (2H, d, J = 8.6Hz), 7.33 (2H, d, J = 8.5Hz), 7.
10 (1H, d, J = 3.8Hz), 6.85 (1H, d, J = 3.8Hz), 4.39 (2H
, s), 4.33 (2H, q, J = 7.2Hz), 3.10-2.92 (2H, m), 1.50
-1.32 (6H, m).

[0399]

Example 131 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone N-methylaminocarbonylhydrazone (Compound No. 1-52)
1) Melting point: 226-229 ° C Mass spectrum (EI) m / e: 399 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.56-7.48
(3H, m), 7.28-7.24 (2H, m), 6.97 (1H, d, J = 3.9Hz), 6.
60 (1H, d, J = 3.8Hz), 6.12 (1H, brd.s), 4.39 (2H, s),
3.00 (2H, q, J = 7.5Hz), 2.94 (3H, d, J = 4.9Hz), 1.42 (3
(H, t, J = 7.5Hz).

[0400]

Example 132 4-chlorophenyl-5-ethylsulfonylmethylthiophen-2-yl ketone = N-methanesulfonylhydrazone (Compound No. 1-527) Physical properties: solid Mass spectrum (EI) m / e: 420 (M ^{+ 1} H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.57 (2H,
d, J = 8.6Hz), 7.37-7.26 (3H, m), 7.03 (1H, d, J = 3.8H
z), 6.73 (1H, d, J = 3.8Hz), 4.38 (2H, s), 3.18 (3H,
s), 3.00 (2H, q, J = 7.6Hz), 1.42 (3H, t, J = 7.5Hz).

[0401]

Working Example 133 4-Chlorophenyl 5-trifluoromethylthiomethylthiophen-2-yl ketone hydrazone (Compound No. 1-579) Physical properties: gum-like mass spectrum (EI) m / e: 350 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.31, 7.6
3 (1H, brd.s, brd.s), 7.61-7.50 (2H, m), 7.33-7.23 (2
H, m), 7.05, 6.76 (1H, d, d, J = 3.6, 3.7Hz), 6.99,
6.56 (1H, d, d, J = 3.6, 3.7Hz), 3.94, 3.85 (2H, s,
s), 3.85, 3.81 (3H, s, s), 2.54, 2.50 (2H, q, q, J = 7.
0, 7.3Hz), 1.70-1.51 (2H, m), 1.00, 0.97 (3H, t, t,
(J = 7.0, 7.3Hz).

[0402]

Working Example 134 4-Chlorophenyl = 5-trifluoromethylthiomethylthiophen-2-yl = ketone = N
-Methoxycarbonylhydrazone (Compound No. 1-58
2) Physical properties: oil Mass spectrum (EI) m / e: 408 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.23, 7.6
5 (1H, s, s), 7.58-7.24 (4H, m), 7.17, 7.02 (1H, d,
d, J = 3.6, 3.6Hz), 6.86, 6.58 (1H, d, d, J = 3.7,3.7H
z), 4.37, 4.29 (2H, s, s), 3.86, 3.83 (3H, s, s).

[0403]

Working Example 135 4-Chlorophenyl = 5- (2,2
2-trifluoroethyl) thiomethylthiophene-2-
Il = ketone = hydrazone (Compound No. 1-584) Physical property: gum Mass spectrum (EI) m / e: 364 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.54-7.26
(4H, m), 7.07 (0.5H, d, J = 3.5Hz), 7.01 (0.5H, d, J = 3.
5Hz), 6.76 (0.5H, d, J = 3.7Hz), 6.41 (0.5H, d, J = 3.7H
z), 5.86 (1H, brd.s), 5.36 (1H, brd.s), 4.09 (1H, s),
3.99 (1H, s), 3.07 (1.5H, q, J = 9.9Hz), 3.01 (1.5H,
q, J = 9.9Hz).

[0404]

Working Example 136 4-Chlorophenyl = 5- (2,2
2-trifluoroethyl) thiomethylthiophene-2-
Il = ketone = N-methoxycarbonylhydrazone (Compound No. 1-587) Physical properties: oil Mass spectrum (EI) m / e: 422 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.27, 7.6
5 (1H, s, s), 7.59-7.54 (2H, m), 7.34-7.26 (2H, m), 7.
11, 7.03 (1H, d, d, J = 3.6, 3.5Hz), 6.80, 6.58 (1H,
d, d, J = 3.7, 3.7Hz), 4.10, 4.00 (2H, s, s), 3.87,
3.83 (3H, s, s), 3.17-2.93 (2H, m).

[0405]

Working Example 137 4-Chlorophenyl 5-propylthiomethylthiophen-2-yl ketone N-methoxycarbonylhydrazone (Compound No. 1-597) Melting point: 79-84 ° C Mass spectrum (EI) m / e: 382 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.31, 7.6
3 (1H, brd.s, brd.s), 7.61-7.50 (2H, m), 7.33-7.23 (2
H, m), 7.05, 6.76 (1H, d, d, J = 3.6, 3.7Hz), 6.99,
6.56 (1H, d, d, J = 3.6, 3.7Hz), 3.94, 3.85 (2H, s,
s), 3.85, 3.81 (3H, s, s), 2.54, 2.50 (2H, q, q, J = 7.
0, 7.3Hz), 1.70-1.51 (2H, m), 1.00, 0.97 (3H, t, t,
(J = 7.0, 7.3Hz).

[0406]

Working Example 138 4-Chlorophenyl 5-isopropylthiomethylthiophen-2-yl ketone N-methoxycarbonylhydrazone (Compound No. 1-602) Melting point: 100-107 ° C Mass spectrum (EI) m / e: 382 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.32, 7.6
2 (1H, brd.s, brd.s), 7.60-7.50 (2H, m), 7.33-7.23 (2
H, m), 7.06, 6.77 (1H, d, d, J = 3.6, 3.7Hz), 6.99,
6.55 (1H, d, d, J = 3.6, 3.7Hz), 3.98, 3.89 (2H, s,
s), 3.85, 3.81 (3H, s, s), 3.05-2.80 (1H, m), 1.31,
1.26 (3H, d, d, J = 6.9Hz).

[0407]

Working Example 139 4-Chlorophenyl 5-tert-
Butylthiomethylthiophen-2-yl = ketone = N-
Methoxycarbonylhydrazone (Compound No. 1-61
2) Melting point: 142-150 ° C Mass spectrum (EI) m / e: 396 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.30, 7.6
0 (1H, brd.s, brd.s), 7.61-7.50 (2H, m), 7.34-7.24 (2
H, m), 7.08, 6.80 (1H, d, d, J = 3.6, 3.7Hz), 6.98,
6.56 (1H, d, d, J = 3.6, 3.7Hz), 4.00, 3.91 (2H, s,
s), 3.85, 3.81 (3H, s, s), 1.38, 1.35 (9H, s, s).

[0408]

Working Example 140 4-Chlorophenyl = 4-chloro-5
-Ethylthiomethylthiophen-2-yl = ketone = N
-Methoxycarbonylhydrazone (Compound No. 1-62)
2) Physical properties: solid Mass spectrum (EI) m / e: 402 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.25, 7.6
8 (1H, s, s), 7.60-7.53 (2H, m), 7.36-7.23 (2H, m),
6.97, 6.51 (1H, s, s), 3.93-3.74 (5H, m), 2.63,2.58
(2H, q, q, J = 7.7, 7.3Hz), 1.31, 1.27 (3H, t, t, J =
(7.7, 7.3Hz).

[0409]

Working Example 141 4-Chlorophenyl 4-bromo-5
-Ethylthiomethylthiophen-2-yl = ketone = N
-Methoxycarbonylhydrazone (Compound No. 1-63
2) Physical properties: solid Mass spectrum (EI) m / e: 446 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.24, 7.6
8 (1H, brd.s, brd.s), 7.60, 7.53 (2H, m), 7.35-7.23
(2H, m), 7.01, 6.55 (1H, s, s), 3.92, 3.84 (2H, s,
s), 3.87, 3.82 (3H, s, s), 2.64, 2.58 (2H, q, q, J =
7.3, 7.3Hz), 1.28, 1.27 (3H, t, t, J = 7.3, 7.3Hz).

[0410]

Example 142 4-Chlorophenyl-5-allylthiomethylthiophen-2-yl ketone = N-methoxycarbonylhydrazone (Compound No. 1-653) Melting point: 125-133 ° C. Mass spectrum (EI) m / e: 380 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.31, 7.6
3 (1H, brd.s, brd.s), 7.61-7.51 (2H, m), 7.35-7.24 (2
H, m), 7.05, 6.76 (1H, d, d, J = 3.5, 3.7Hz), 7.00,
6.57 (1H, d, d, J = 3.5, 3.7Hz), 5.88-5.68 (1H, m), 5.
20-5.04 (2H, m), 3.89, 3.86 (2H, s, s), 3.81, 3.80 (3
H, s, s), 3.18, 3.13 (2H, d, d, J = 7.1, 7.1Hz).

[0411]

Working Example 143 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone (Compound No. 3-
4) Melting point: 53-55 ° C Mass spectrum (EI) m / e: 296 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.80 (2H,
d, J = 8.6Hz), 7.47 (2H, d, J = 8.6Hz), 7.47 (1H, d, J = 3.
9Hz), 7.02 (1H, d, J = 3.8Hz), 3.95 (2H, s), 2.57 (2H,
q, J = 7.5Hz), 1.28 (3H, t, J = 7.4Hz).

[0412]

Example 144 4-Chlorophenyl 5-ethylsulfonylmethylthiophen-2-yl ketone (Compound No. 3-6) Melting point: 145-146 ° C. Mass spectrum (EI) m / e: 328 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.82 (2H,
d, J = 8.6Hz), 7.57 (1H, d, J = 3.9Hz), 7.49 (2H, d, J = 8.
6Hz), 7.27 (1H, d, J = 3.6Hz), 4.47 (2H, s), 3.02 (2H,
q, J = 7.5Hz), 1.43 (3H, t, J = 7.5Hz).

[0413]

Working Example 145 4-Chlorophenyl-5-trifluoromethylthiophen-2-yl ketone (Compound No. 3)
-7) Melting point: 67-68 ° C Mass spectrum (EI) m / e: 336 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.83-7.78
(2H, m), 7.51-7.46 (3H, m), 7.11 (1H, d, J = 3.7Hz), 4.
35 (2H, s).

[0414]

Working Example 146 4-Chlorophenyl 5-propylthiomethylthiophen-2-yl ketone (Compound No. 3)
-13) Physical properties: oil Mass spectrum (EI) m / e: 310 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.80 (2H,
d, J = 8.6Hz), 7.47 (1H, d, J = 3.9Hz), 7.47 (2H, d, J = 8.
6Hz), 7.01 (1H, d, J = 3.9Hz), 3.92 (2H, s), 2.53 (2H,
t, J = 7.4Hz), 1.72-1.53 (2H, m), 0.99 (3H, t, J = 7.2H
z).

[0415]

Working Example 147 4-Chlorophenyl 5-isopropylthiomethylthiophen-2-yl ketone (Compound No. 3-15) Physical properties: oil Mass spectrum (EI) m / e: 310 (M ⁺ ), 250, 235 ^{, 207. 1 H-NMR (200MHz} , CDCl 3) spectrum δ (ppm): 7.80 (2H ,
d, J = 8.6Hz), 7.47 (2H, d, J = 8.6Hz), 7.46 (1H, d, J = 3.
8Hz), 7.02 (1H, d, J = 3.8Hz), 3.96 (2H, s), 2.95 (1H,
heptet, J = 6.7Hz), 1.29 (6H, d, J = 6.7Hz).

[0416]

Working Example 148 4-Chlorophenyl 5-tert-
Butylthiomethylthiophen-2-yl = ketone (Compound No. 3-19) Melting point: 80-81 ° C Mass spectrum (EI) m / e: 324 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.79 (2H,
d, J = 8.6Hz), 7.48 (1H, d, J = 3.8Hz), 7.46 (2H, d, J = 8.
6Hz), 7.05 (1H, d, J = 3.8Hz), 3.98 (2H, s), 1.37 (9H,
s).

[0417]

Example 149 4-Chlorophenyl-5-allylthiomethylthiophen-2-yl ketone (Compound No. 3-
41) Melting point: 47-48 ° C Mass spectrum (EI) m / e: 308 (M ⁺ ). ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.80 (2H,
d, J = 8.5Hz), 7.47 (2H, d, J = 8.5Hz), 7.47 (1H, d, J = 3.
8Hz), 7.01 (1H, d, J = 3.8Hz), 5.90-5.70 (1H, m), 5.20
-5.07 (2H, m), 3.87 (2H, s), 3.16 (2H, d, J = 7.2Hz).

[0418]

Example 150 4-chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-methyl-N
-Acetylhydrazone (Compound No. 1-1833) Melting point: 38-56 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.45 (2H,
d, J = 8.3Hz), 7.30 (2H, d, J = 8.3Hz), 6.81 (2H, d, J = 3.
5Hz), 6.64 (2H, d, J = 3.5Hz), 3.89 (2H, s), 2.75 (3H,
s), 2.54 (2H, q, J = 3.4Hz), 2.34 (3H, s), 1.26 (3H, t,
J = 3.4Hz).

[0419]

Example 151 4-chlorophenyl-5- (ethylthio-1-ethyl) thiophen-2-yl ketone = N-
Ethoxycarbonylhydrazone (Compound No. 1-183)
4) Physical properties: Oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.29 (1H,
brd.s), 7.55 (2H, m), 7.29 (2H, m), 7.05, 6.99 (1H,
d, d, J = 3.6, 3.6Hz), 6.76, 6.54 (1H, d, d, J = 3.6,
3.6), 4.31-4.10 (3H, m), 2.55, 2.46 (2H, q, q, J = 7.
2, 7.7Hz), 1.70, 1.63 (3H, d, d, J = 7.1, 6.9Hz), 1.3
6-1.18 (6H, m).

[0420]

Working Example 152 4-Methoxycarbonylphenyl = 5
-Ethylthiomethylthiophen-2-yl = ketone = N
-Ethoxycarbonylhydrazone (Compound No. 1-18
35) Melting point: 100-110 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.59, 8.2
7 (1H, s, s), 7.11-7.56 (3H, m), 6.77, 7.10 (1H, d,
d, J = 3.7, 3.7Hz), 6.56, 7.07 (1H, d, d, J = 3.7,3.7H
z), 4.21-4.36 (2H, s), 3.87, 3.92 (2H, s, s), 2.48-
2.67 (2H, m), 1.21-1.38 (6H, m).

[0421]

Working Example 153 4- (2,2,2-trifluoroethylaminocarbonyl) phenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-ethoxycarbonylhydrazone (Compound No. 1-1836) Physical property: solid Mass spectrum (EI) m / e: 473 (M ⁺ ), 412, 371, 340, 32
^{5. 1 H-NMR (200MHz,} CDCl 3) spectrum δ (ppm): 7.55, 8.3
9 (1H, s, s), 7.77, 8.02 (2H, d, d, J = 8.7, 8.7Hz),
7.43, 7.70 (2H, d, d, J = 8.7, 8.7Hz), 6.76, 7.07 (1H,
d, d, J = 3.7, 3.7Hz), 6.52, 7.01 (1H, d, d, J = 3.7,
3.7Hz), 4.05-4.37 (4H, m), 3.87, 3.98 (2H, s, s), 2.
47-2.69 (2H, m), 1.21-1.38 (6H, m).

[0422]

Example 154 4-methoxyphenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylhydrazone (Compound No. 1-1837) Physical properties: Oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.73, 7.6
1 (1H, brd.s, brd.s), 7.60-6.75 (5H, m), 6.99, 6.61
(1H, d, d, J = 3.7, 3.7Hz), 4.31-4.20 (2H, m), 3.96-
3.82 (5H, m), 2.61, 2.54 (2H, q, q, J = 7.3, 7.3Hz),
1.33-1.20 (6H, m).

[0423]

Example 155 4-methoxyphenyl-5-ethylsulfinylmethylthiophen-2-yl ketone = N-
Ethoxycarbonylhydrazone (Compound No. 1-183)
8) Physical properties: solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.18, 7.7
8 (1H, brd.s, brd.s), 7.60-6.68 (6H, m), 4.31-4.14 (2
H, m), 4.12, 3.89 (3H, s, s), 3.89, 3.82 (2H, s, s),
2.80-2.55 (2H, m), 1.42-1.22 (6H, m).

[0424]

Working Example 156 4-Methylphenyl 5-ethylthiomethylthiophen-2-yl ketone N-ethoxycarbonylhydrazone (Compound No. 1-1839) Physical properties: Oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.25, 7.7
0 (1H, brd.s, br.s), 7.55-6.74 (5H, m), 6.99, 6.59 (1
(H, d, d, J = 3.7, 3.7Hz), 4.35-4.17 (2H, m), 3.96, 3.
87 (2H, s, s), 2.60, 2.54 (2H, q, q, J = 7.3, 7.3Hz),
2.44, 2.36 (3H, s, s), 1.37-1.20 (6H, m).

[0425]

Working Example 157 4-Methylphenyl 5-ethylsulfinylmethylthiophen-2-yl ketone N-ethoxycarbonylhydrazone (Compound No. 1-184)
0) Physical properties: solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.23, 7.7
5 (1H, brd.s, brd.s), 7.50-6.87 (5H, m), 7.12, 6.68
(1H, d, d, J = 3.6, 3.6Hz), 4.35-4.09 (4H, m), 2.80-
2.55 (2H, m), 2.45, 2.36 (3H, s, s), 1.42-1.23 (6H,
m).

[0426]

Working Example 158 4-trifluoromethylphenyl = 5
-Ethylthiomethylthiophen-2-yl = ketone = N
-Ethoxycarbonylhydrazone (Compound No. 1-18
41) Physical properties: solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.36-7.46
(5H, m), 7.08, 6.77 (1H, d, d, J = 3.7, 3.7Hz), 7.02,
6.53 (1H, d, d, J = 3.7, 3.7Hz), 4.37-4.20 (2H, m), 3.
98, 3.88 (2H, s, s), 2.61, 2.54 (2H, q, q, J = 7.3, 7.
3Hz), 1.38-1.21 (6H, m).

[0427]

Working Example 159 4-trifluoromethylphenyl = 5
-Ethylsulfinylmethylthiophen-2-yl = ketone = N-ethoxycarbonylhydrazone (Compound No. 1-1842) Physical properties: solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.33-7.46
(5H, m), 7.23, 6.89 (1H, d, d, J = 3.7, 3.7Hz), 7.15,
6.62 (1H, d, d, J = 3.7, 3.7Hz), 4.37-4.03 (4H, m), 2.
81-2.55 (2H, m), 1.43-1.26 (6H, m).

[0428]

Example 160 4-trifluoromethoxyphenyl =
5-ethylthiomethylthiophen-2-yl = ketone =
N-ethoxycarbonylhydrazone (Compound No. 1-1
843) Physical properties: solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.30, 7.5
9 (1H, brd.s, brd.s), 7.70-7.16 (4H, m), 7.07, 6.77
(1H, d, d, J = 3.7, 3.7Hz), 7.01, 6.55 (1H, d, d, J =
3.7, 3.7Hz), 4.31, 4.27 (2H, q, q, J = 7.3, 7.3Hz),
3.97, 3.87 (2H, s, s), 2.61, 2.53 (2H, q, q, J = 7.3,
(7.3Hz), 1.38-1.21 (6H, m).

[0429]

Example 161 4-trifluoromethoxyphenyl =
5-ethylsulfinylmethylthiophen-2-yl =
Ketone = N-ethoxycarbonylhydrazone (Compound No. 1-1844) Physical property: solid ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.27-7.16
(5H, m), 7.22, 6.89 (1H, d, d, J = 3.7, 3.7Hz), 7.14,
6.64 (1H, d, d, J = 3.7, 3.7Hz), 4.36-4.07 (4H, m), 2.
81-2.56 (2H, m), 1.43-1.26 (6H, m).

[0430]

Working Example 162 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (2,4-
Dimethyl-2H-pyrazol-3-yl) carbonylhydrazone (Compound No. 1-1845) Melting point: 110-120 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.49, 8.3
3 (1H, brd.s, brd.s), 7.60 (2H, brd.d, J = 6.7Hz), 7.3
4 (2H, brd.d, J = 6.7Hz), 7.15, 5.85 (1H, brd.s, brd.
s), 6.81 (1H, m), 6.33 (1H, m), 4.12 (3H, m), 3.90 (2
H, s), 2.55 (1H, q, J = 7.5Hz), 2.30 (3H, m), 1.26 (3H,
t, J = 7.5Hz).

[0431]

Working Example 163 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (furan-
2-yl) carbonylhydrazone (Compound No. 1-18)
46) Melting point: 116-120 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.12, 8.3
9 (1H, brd.s, brd.s), 7.84-7.12 (6H, m), 6.81 (1H, d,
J = 3.5Hz), 6.69-6.49 (2H, m), 4.01, 3.90 (2H, s, s),
2.58 (2H, m), 1.29 (3H, m).

[0432]

Example 164 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N- (2-carboxybenzoyl) hydrazone (Compound No. 1-184)
7) Melting point: 146-156 ° C. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 9.18, 8.6
7 (1H, brd.s, brd.s), 8.09 (1H, t, J = 7.6Hz), 7.68 (1
H, t, J = 7.6Hz), 7.54-7.00 (7H, m), 6.67, 6.44 (1H,
d, d, J = 3.5, 3.5Hz), 3.96, 3.76 (2H, s, s), 2.56,
2.45 (2H, q, q, J = 7.3, 7.6Hz), 1.29, 1.22 (3H, t, t,
(J = 7.6, 7.3Hz).

[0433]

Working Example 165 4-Chlorophenyl = 5-ethylthiomethylthiophen-2-yl = ketone = N-carboxyethylcarbonylhydrazone (Compound No. 1-184)
8) ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.95, 8.5
6 (1H, s, s), 7.57-7.25 (4H, m), 7.04, 7.00 (1H, d,
d, J = 3.6, 3.5Hz), 6.77, 6.55 (1H, d, d, J = 3.6,3.5H
z), 3.95, 3.89 (2H, s, s), 3.11 (2H, m), 2.74 (2H,
m), 1.29 (5H, m).

[0434]

Example 166 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylaminocarbonylhydrazone (Compound No. 1-
1849) Melting point: 168-171 ° C. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 10.7 (1H,
s), 8.53, 7.69 (1H, s, s), 7.54 (2H, m), 7.30 (2H, m),
6.79 (1H, d, J = 3.6Hz), 6.64 (1H, d, J = 3.6Hz), 4.31-
4.12 (2H, m), 3.90, 3.87 (2H, s, s), 2.53 (2H, q, J =
7.4Hz), 1.37-1.24 (6H, m).

[0435]

Example 167 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylmethylaminocarbonylhydrazone (Compound No. 1-1850) Melting point: 137-141 ° C. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.53 (2H,
d, J = 8.5Hz), 7.28 (2H, d, J = 8.5Hz), 6.76 (1H, d, J = 3.
6Hz), 6.67 (1H, t, J = 5.6Hz), 6.51 (1H, d, J = 3.6Hz),
4.29-4.17 (2H, m), 4.13 (2H, d, J = 5.6Hz), 2.54 (2H, m
q, J = 7.5Hz), 1.29 (6H, m).

[0436]

Example 168 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N- (3-ethoxycarbonyl-trans-acryloyl) hydrazone (Compound No. 1-11851) Melting point: 117-124 ° C. ¹ H -NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.44 (1H,
s), 7.98 (1H, d, J = 15.7Hz), 7.55 (2H, d, J = 8.0Hz),
7.28 (2H, d, J = 8.0Hz), 6.96 (1H, d, J = 15.7Hz), 6.79 (1
H, d, J = 3.7Hz), 6.60 (1H, d, J = 3.7Hz), 4.31 (2H, q,
J = 7.0Hz), 3.89 (2H, s), 2.55 (2H, q, J = 7.2Hz), 1.36
(3H, t, J = 7.2Hz), 1.27 (3H, t, J = 7.0Hz).

[0437]

Working Example 169 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (3-ethoxycarbonyl-cis-acryloyl) hydrazone (Compound No. 1-1852) Melting point: 150-154 ° C. ¹ H -NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.60 (1H,
brd.s), 7.60 (2H, d, J = 8.4Hz), 7.53 (1H, d, J = 13.2H
z), 7.30 (2H, d, J = 8.4Hz), 6.82 (1H, d, J = 3.9Hz), 6.
60 (1H, d, J = 3.9Hz), 6.60 (1H, d, J = 13.2Hz), 3.91 (2
H, s), 2.56 (2H, q, J = 7.7Hz), 1.28 (3H, t, J = 7.7Hz).

[0438]

Example 170 C- (4-chlorophenyl) -C-
(5-ethylthiomethylthiophen-2-yl) methyleneamino-N-isoindole-1,3-dione (Compound No. 1-1853) (one geometric isomer) Physical property: solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) Spectrum δ (ppm): 8.10-7.25
(8H, m), 6.94 (2H, m), 3.92 (2H, s), 2.57 (2H, m), 1.2
8 (3H, t, J = 7.6Hz). (Other geometric isomers) Physical properties: Solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.79-7.91
(2H, m), 7.75 (2H, m), 7.41 (4H, m), 6.91 (2H, m), 3.9
8, 3.92 (2H, s, s), 2.58 (2H, m), 1.29 (3H, m).

[0439]

Working Example 171 C- (4-Chlorophenyl) -C-
(5-ethylthiomethylthiophen-2-yl) methyleneamino-N-pyrrolidine-2,5-dione (Compound No. 1-1854) (one geometric isomer) Physical property: solid-state ¹ H-NMR (200 MHz, CDCl ₃₎ ) Spectrum δ (ppm): 7.38 (2H,
d, J = 8.6Hz), 7.27 (2H, d, J = 8.6Hz), 6.90 (2H, m), 3.9
0 (2H, s), 2.57 (4H, s), 2.54 (2H, q, J = 7.7Hz), 1.26
(3H, t, J = 7.7 Hz). (Other geometric isomers) Melting point: 135-150 ° C. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.69 (2H,
d, J = 8.4Hz), 7.40 (2H, d, J = 8.4Hz), 7.01 (1H, d, J = 3.
8Hz), 6.91 (1H, d, J = 3.8Hz), 3.90 (2H, s), 2.81 (4H,
s), 2.52 (2H, q, J = 7.4Hz), 1.28 (3H, t, J = 7.4Hz).

[0440]

Working Example 172 C- (4-chlorophenyl) -C-
(5-Ethylthiomethylthiophen-2-yl) methyleneamino-N-pyrrole-2,5-dione (Compound No. 1-1855) Properties: Solid-state ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.10-7.9
0, 7.64-7.54, 7.16-6.85, 6.70-6.50 (4H, m, m, m,
m), 7.50-7.39 (2H, m), 7.38-7.22 (2H, m), 4.00-3.86
(2H, m), 2.67-2.51 (2H, m), 1.36-1.22 (3H, m).

[0441]

Example 173 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethylidenehydrazone (Compound No. 1-1856) Physical property: Oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ ppm): 8.00-7.95
(1H, m), 5.58-7.23 (4H, m), 7.01-6.75 (2H, m), 3.94,
3.89 (2H, m), 2.54-2.52 (2H, m), 2.23, 1.99 (3H, d,
d, J = 5.7, 5.7Hz), 1.29-1.24 (3H, m).

[0442]

EXAMPLE 174 4-chlorophenyl = 5-ethyl-thio-methylthiophene-2-yl = ketone = N-(1-chloro-ethylidene) hydrazone (Compound No. 1-1857) Physical properties: oil ¹ H-NMR (200MHz, CDCl ₃ ) Spectrum δ (ppm): 7.62, 7.5
9 (1H, s, s), 7.40, 7.39 (2H, d, d, J = 5.0, 5.0Hz),
7.25, 7.24 (2H, d, d, J = 5.0, 5.0Hz), 7.05-6.81 (1H,
m), 3.94, 3.89 (2H, s, s), 2.60, 2.31 (3H, s, s), 2.
58-2.52 (2H, m), 1.27 (3H, t, J = 6.7Hz).

[0443]

Working Example 175 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (1-methylethylidene) hydrazone (Compound No. 1-1858) Properties: Oil ¹ H-NMR (200 MHz, CDCl) ₃ ) Spectrum δ (ppm): 7.56-7.23
(4H, m), 6.99-6.72 (2H, m), 3.93-3.86 (2H, m), 2.61-
2.53 (2H, m), 2.24, 2.05, 2.03, 1.95 (6H, s, s, s,
s), 1.29-1.23 (3H, m).

[0444]

EXAMPLE 176 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N- (ethoxyethyleneaminomethylidene) hydrazone (Compound No. 1)
-1859) Physical properties: Oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.55-7.50
(2H, m), 7.37, 7.36 (2H, d, d, J = 7.4, 5.6Hz), 6.99-
6.96 (1H, m), 6.84-6.82 (1H, m), 3.94 (2H, s), 3.80-3.
73 (2H, m), 3.59-3.41 (4H, m), 2.53 (2H, q, J = 6.9Hz),
2.25, 2.24 (3H, s, s), 1.26,1.25 (3H, t, t, J = 6.6,
6.6Hz), 1.18 (3H, t, J = 6.9Hz).

[0445]

Example 177 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (dimethylaminomethylidene) hydrazone (Compound No. 1-186)
0) Physical properties: Oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.56-7.34
(4H, m), 6.97, 6.78 (1H, d, d, J = 3.9, 3.9Hz), 6.84,
6.61 (1H, d, d, J = 3.9, 3.9Hz), 3.95, 3.89 (2H, s,
s), 3.22 (3H, s), 2.89 (3H, s), 2.57-2.51 (2H, s), 2.
38, 2.33 (3H, s, s), 1.29-1.23 (3H, m).

[0446]

Example 178 4-Chlorophenyl 5-ethylthiomethylthiophen-2-yl ketone N- (methoxyethyleneaminomethylidene) hydrazone (Compound No. 1)
-1861) Physical properties: oil ^{1 H-NMR (200MHz, CDCl} 3) spectrum δ (ppm): 7.54-7.35
(4H, m), 6.98-6.54 (2H, m), 4.13, 4.11 (2H, s, s), 3.
82-3.34 (4H, m), 3.42, 3.35 (3H, s, s), 2.59-2.54 (2
H, m), 1.29, 1.26 (3H, t, t, J = 7.3, 7.3Hz).

[0447]

Example 179 4-Chlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N- (methoxypropyleneaminomethylidene) hydrazone (Compound No. 1-1862) (one geometric isomer) Physical property: oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.55-7.35
(4H, m), 6.99-6.84 (2H, m), 3.94, 3.89 (2H, s, s), 3.
73-3.31 (4H, m), 3.42, 3.30 (3H, s, s), 2.54 (2H, q,
J = 7.4Hz), 2.23, 1.98 (3H, s, s), 1.86-1.78 (2H, m),
1.25 (3H, t, J = 7.4Hz) ( Other geometric isomers) Physical properties:. Oil ^{1 H-NMR (200MHz, CDCl} 3) spectrum δ (ppm): 7.51-7.37
(4H, m), 6.90-6.63 (2H, m), 3.94, 3.89 (2H, s, s), 3.
73-3.31 (4H, m), 3.42, 3.30 (3H, s, s), 2.54 (2H, q,
J = 7.4Hz), 2.23, 1.98 (3H, s, s), 1.86-1.74 (2H, m),
1.26 (3H, t, J = 7.4Hz).

[0448]

Working Example 180 3,5-Dichlorophenyl-5-ethylthiomethylthiophen-2-yl ketone = N-ethoxycarbonylhydrazone (Compound No. 5-1) Mass spectrum (EI) m / e: 416 (M ⁺ ) , 355, 283, 253. Physical properties: Oil ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.32 (1H,
s), 7.20-7.58 (3H, m), 6.78, 7.08 (1H, d, d, J = 3.7H
z), 6.55, 7.00 (1H, d, d, J = 3.7Hz), 4.30 (2H, m), 3.
87, 3.98 (2H, s, s), 2.47-2.67 (4H, m), 1.11-1.14 (6
H, m).

[0449]

Working Example 181 3,5-Dichlorophenyl = 5-ethylsulfinylmethylthiophen-2-yl = ketone =
N-ethoxycarbonylhydrazone (Compound No. 5-
2) (one geometric isomer) Melting point: 164-166 ° C ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.56 (1H,
t, J = 1.8Hz), 7.21 (2H, d, J = 1.8Hz), 7.04 (1H, d, J = 3.
7Hz), 6.67 (1H, d, J = 3.7Hz), 4.38 (2H, s), 4.28 (2H,
q, J = 7.3Hz), 2.97 (2H, q, J = 7.7Hz), 1.40 (3H, t, J =
(7.3 Hz), 1.36 (3H, t, J = 7.7 Hz). (Other geometric isomers) Melting point: 152-153 ° C. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 8.25 (1H,
s), 7.48 (2H, d, J = 1.8Hz), 7.26-7.37 (2H, m), 7.15 (1
H, d, J = 3.7Hz), 4.48 (2H, s), 4.32 (2H, q, J = 7.3Hz),
3.06 (2H, q, J = 7.0Hz), 1.46 (3H, t, J = 7.3Hz), 1.35
(3H, t, J = 7.0Hz).

[0450]

Working Example 182 2,4-Difluorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-ethoxycarbonylhydrazone (Compound No. 5-3) Melting point: 105-109 ° C. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.52 (1H,
s), 7.33-7.19 (1H, m), 7.11-6.96 (2H, m), 6.78 (1H, d,
J = 3.7Hz), 6.57 (1H, d, J = 3.7Hz), 4.28 (2H, q, J = 3.7
Hz), 3.87 (2H, s), 2.54 (2H, q, J = 4.0Hz), 1.33 (3H,
t, J = 4.0Hz), 1.25 (3H, t, J = 3.7Hz).

[0451]

Working Example 183 3,4-Difluorophenyl 5-ethylthiomethylthiophen-2-yl ketone N-ethoxycarbonylhydrazone (Compound No. 5-4) Melting point: 92-98 ° C. ¹ H-NMR (200 MHz, CDCl ₃ ) spectrum δ (ppm): 7.59, 8.2
7 (1H, s, s), 7.11-7.56 (3H, m), 6.77, 7.10 (1H, d,
d, J = 3.7, 3.7Hz), 6.56, 7.07 (1H, d, d, J = 3.7,3.7H
z), 4.21-4.36 (2H, m), 3.87, 3.97 (2H, s, s), 2.48-
2.66 (2H, m), 1.21-1.38 (6H, m). In the following formulation examples,% indicates% by weight unless otherwise specified.

[0452]

Formulation Example 1 Emulsion 5% of the compound of Example 1 (Compound No. 1-344) was dissolved in 85% of a 1: 1 mixed solution of xylene-dimethylsulfoxod, and then alkylphenol ethylene oxide condensate and alkylbenzene sulfone were added thereto. 10% of a mixture of calcium acid (8: 2) was mixed to obtain an emulsion. The drug is diluted with water and used as a spray liquid.

[0453]

Formulation Example 2 Wettable powder 20% of the compound of Example 1 (compound No. 1-344), 35% of kaolin and 30% of clay, and 7.5% of diatomaceous earth are mixed, and further, 30% of sodium laurate and dinaphthylmethane are mixed. A wettable powder is obtained by mixing 7.5% of a mixture (1: 1) of sodium sulfonate and pulverizing. The drug is diluted with water and used as a spray liquid.

[0454]

[Formulation Example 3] Powder 1% of the compound of Example 1 (Compound No. 1-344) and 97% of a talc-calcium carbonate mixture (1: 1) are mixed and ground, sufficiently uniformly dispersed and blended, and then silicic anhydride is further added. Add 2%, mix and pulverize to obtain a powder. Spray this agent as it is.

[0455]

Formulation Example 4 Granules After mixing 2% of the compound of Example 1 (Compound No. 1-344), 48% of bentonite fine powder, 48% of talc and 2% of sodium ligninsulfonate, water is added to make the mixture uniform. And then granulated and dried to obtain a particle size of 0.6.
~ 1.0 mm granules are obtained. Spray this agent as it is on the soil surface.

[0456]

Formulation Example 5 Oil 0.1% of the compound of Example 1 (Compound No. 1-344) and 0.5% of piperonyl butoxide are mixed and dissolved in 99.4% of white kerosene to obtain an oil.

[0457]

[Test Example 1] Insecticidal test of Japanese moth insect A 5% emulsion of the compound of the present invention was prepared according to Formulation Example 1, and diluted with water so as to have an active ingredient of 200 ppm. 20)
Add so as to make a 00-fold dilution. ｝. The cabbage leaves were immersed in this solution for 20 seconds, air-dried, and then placed in a 250 ml plastic cup. 10 larvae of the third instar larva
The head was released and placed in a constant temperature room at 25 ° C. Five days after the treatment, the number of dead insects was examined, and the mortality was calculated.

For comparison, see Japanese Patent Application Laid-Open No. 1-50193.
No. 5 compound of compound No. 477 (Comparative compound a)
A similar test was performed for Compound No. 478 (Comparative Compound b). Comparative compound a: (phenyl-2-thienylmethylene) hydrazinecarboxylic acid ethyl ester. Comparative compound b: (phenyl-2-thienylmethylene) hydrazinecarboxylic acid methyl ester.

In this test, compounds showing a mortality of 90% were obtained from Example 1 (Compound No. 1-344), Example 2 (Compound No. 1-1), and Example 3 (Compound No. 1-2). Example 4 (Compound No. 1-345), Example 5 (Compound No. 1-101), Example 6 (Compound No. 1-131),
Example 7 (Compound No. 1-242), Example 12 (Compound No. 2-9), Example 13 (Compound No. 1-3), Example 14 (Compound No. 1-4), Example 15 (Compound No. 1-5), Example 16 (Compound No. 1-6), Example 17 (Compound No. 1-13), Example 18 (Compound No. 1-15), Example 19 (Compound No. 1-16), Example Example 20 (Compound No. 1-17), Example 21 (Compound No. 1-18), Example 22 (Compound No. 1-19), Example 23 (Compound No. 1-20), Example 24 (Compound No. 1) -31), Example 25 (Compound No. 1-33),
Example 26 (Compound No. 1-37), Example 27 (Compound No. 1-41), Example 28 (Compound No. 1-4)
4), Example 29 (Compound No. 1-46), Example 30
(Compound No. 1-48), Example 31 (Compound No. 1-
50), Example 32 (Compound No. 1-51), Example 3
3 (Compound No. 1-56), Example 34 (Compound No. 1)
-57), Example 35 (Compound No. 1-58), Example 36 (Compound No. 1-60), Example 37 (Compound No. 1-62), Example 38 (Compound No. 1-63), Example 39 (Compound No. 1-65), Example 40 (Compound No. 1-68), Example 41 (Compound No. 1-73), Example 42 (Compound No. 1-88), Example 48 (Compound No. 1-68) 145), Example 49 (Compound No. 1-14)
6), Example 50 (Compound No. 1-147), Example 5
1 (Compound No. 1-148), Example 52 (Compound No. 1-157), Example 53 (Compound No. 1-160),
Example 54 (Compound No. 1-162), Example 55 (Compound No. 1-163), Example 56 (Compound No. 1-1)
64), Example 57 (Compound No. 1-174), Example 58 (Compound No. 1-184), Example 59 (Compound No. 1-188), Example 60 (Compound No. 1-18)
9), Example 61 (Compound No. 1-199), Example 6
2 (Compound No. 1-200), Example 63 (Compound No. 1-201), Example 64 (Compound No. 1-204),
Example 65 (Compound No. 1-206), Example 66 (Compound No. 1-207), Example 67 (Compound No. 1-2)
09), Example 68 (Compound No. 1-229), Example 69 (Compound No. 1-232), Example 70 (Compound No. 1-233), Example 71 (Compound No. 1-28)
8), Example 72 (Compound No. 1-290), Example 7
3 (Compound No. 1-291), Example 74 (Compound No. 1-292), Example 75 (Compound No. 1-293),
Example 76 (Compound No. 1-294), Example 77 (Compound No. 1-303), Example 78 (Compound No. 1-3)
04), Example 79 (Compound No. 1-306), Example 80 (Compound No. 1-307), Example 81 (Compound No. 1-308), Example 82 (Compound No. 1-30)
9), Example 83 (Compound No. 1-314), Example 8
4 (Compound No. 1-319), Example 85 (Compound No. 1-321), Example 86 (Compound No. 1-333),
Example 87 (Compound No. 1-334), Example 88 (Compound No. 1-336), Example 89 (Compound No. 1-3)
39), Example 90 (Compound No. 1-346), Example 91 (Compound No. 1-348), Example 92 (Compound No. 1-351), Example 93 (Compound No. 1-35)
3), Example 94 (Compound No. 1-354), Example 9
5 (Compound No. 1-356), Example 96 (Compound No. 1-360), Example 97 (Compound No. 1-373),
Example 98 (Compound No. 1-376), Example 99 (Compound No. 1-379), Example 100 (Compound No. 1-376)
384), Example 101 (Compound No. 1-400), Example 102 (Compound No. 1-401), Example 103
(Compound No. 1-403), Example 104 (Compound No. 1-404), Example 105 (Compound No. 1-40)
9), Example 106 (Compound No. 1-437), Example 107 (Compound No. 1-438), Example 108 (Compound No. 1-439), Example 109 (Compound No. 1-4)
40), Example 110 (Compound No. 1-447), Example 111 (Compound No. 1-449), Example 112 (Compound No. 1-452), Example 113 (Compound No. 1-4)
453), Example 114 (Compound No. 1-455), Example 115 (Compound No. 1-457), Example 116
(Compound No. 1-466), Example 117 (Compound No. 1-468), Example 118 (Compound No. 1-47)
6), Example 119 (Compound No. 1-479), Example 120 (Compound No. 1-481), Example 121 (Compound No. 1-484), Example 122 (Compound No. 1-4)
86), Example 123 (Compound No. 1-491), Example 125 (Compound No. 1-493), Example 125 (Compound No. 1-495), Example 126 (Compound No. 1-49)
496), Example 127 (Compound No. 1-498), Example 128 (Compound No. 1-499), Example 129
(Compound No. 1-501), Example 130 (Compound No. 1-518), Example 131 (Compound No. 1-52)
1), Example 132 (Compound No. 1-527), Example 133 (Compound No. 1-579), Example 134 (Compound No. 1-582), Example 135 (Compound No. 1-5)
84), Example 136 (Compound No. 1-587), Example 137 (Compound No. 1-597), Example 138 (Compound No. 1-602), Example 139 (Compound No. 1-587).
612), Example 140 (Compound No. 1-622), Example 141 (Compound No. 1-632) and Example 142.
(Compound No. 1-653), and Comparative Compounds a and b had a mortality of 0%.

[0460]

[Test Example 2] Insecticidal test of brown planthoppers A 5% emulsion of the compound of the present invention was prepared according to Preparation Example 1, and diluted with water so that the active ingredient content was 200 ppm. 20)
Add so as to make a 00-fold dilution. ｝. Rice foliage was immersed in this solution for 20 seconds, air-dried, fixed in a glass cylinder, and the root was immersed in water. One third-instar larva of brown planthopper in a cylinder
0 animals were released, covered with a paper envelope, and placed in a constant temperature room at 25 ° C. Six days after the treatment, the number of dead insects was examined, and the mortality was calculated.

As in Test Example 1, comparative compounds a and b were tested for comparison.

In this test, compounds showing a mortality of 100% were obtained from Example 1 (Compound No. 1-344), Example 4 (Compound No. 1-345), and Example 104 (Compound No. 1-344).
404), Example 105 (Compound No. 1-409) and Example 138 (Compound No. 1-602), and Comparative Compounds a and b had a mortality of 0%.

[0463]

Test Example 3 Cotton Aphid Insecticidal Test A cucumber leaf leaf disk (4.5 cm × 4.5 cm) was placed on absorbent cotton moistened with water, and adult cotton aphids were released. After 18 hours of littering, the adults were removed and the number of larvae was adjusted to 10 per leaf disk. A 5% emulsion of the compound of the present invention is prepared according to Formulation Example 1, and diluted with water so that the active ingredient becomes 200 ppm. So added. ｝, 2ml of this drug solution
Was sprayed on the leaf disk using a rotary spray tower.
After air-drying, the leaf disk was placed in a sealed container and placed in a constant temperature room at 25 ° C. Five days after the treatment, the number of dead insects was investigated, and the mortality was calculated.

As a comparison, Comparative Compound b was tested.

In this test, compounds showing a mortality of 100% were obtained from Example 2 (Compound No. 1-1), Example 4 (Compound No. 1-345), and Example 12 (Compound No. 2-9). ,
Example 14 (Compound No. 1-4), Example 21 (Compound No. 1-18), Example 35 (Compound No. 1-58),
Example 73 (Compound No. 1-291), Example 83 (Compound No. 1-314), Example 84 (Compound No. 1-3)
19), Example 90 (Compound No. 1-346), Example 91 (Compound No. 1-348), Example 93 (Compound No. 1-353), Example 95 (Compound No. 1-35)
6), Example 101 (Compound No. 1-400), Example 102 (Compound No. 1-401), Example 104 (Compound No. 1-404), Example 105 (Compound No. 1-40)
9), Example 116 (Compound No. 1-466), Example 119 (Compound No. 1-479) and Example 125 (Compound No. 1-493), and Comparative Compound b is
The mortality was 40%.

[0466]

EFFECTS OF THE INVENTION The heteroarylhydrazone compound of the present invention is a compound of the class Hemiptera, Lepidoptera, Coleoptera, Diptera, Hymenoptera, Orthoptera, Termites, Thripidae, It shows an excellent control effect on a wide range of pests such as spider mites and plant parasitic nematodes, and can also control pests having resistance to existing pesticides.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 333/24 C07D 333/24 333/28 333/28 333/32 333/32 333/38 333/38 409 / 12 409/12 (72) Inventor Hideshi Okui 1041, Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture In-house (72) Inventor Mitsuru Ito 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture In-house Sankyo Co., Ltd. (72) Reiji Ichinose, inventor 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Stock Company In-house (72) Inventor Seiichiro Kodama 6-8-22-401 Kamiochiai, Yono-shi, Saitama (72) Inventor Atsushi Iwabuchi 5-1857-6, Mitsuhashi, Omiya-shi, Saitama F-term (Reference) 4C023 DA02 DA06 EA08 FA03 HA04 4C063 AA01 BB09 CC92 DD07 DD22 DD75 EE03 4C069 AC06 AC30 4H011 AC01 AC02 AC03 AC04 AC05 BA01 BB08 BB09 BC01 BC03 BC06 BC07 BC18 BC20 DA02 DA15 DA16

Claims (23)

[Claims] 1. A compound represented by the following general formula (I): [Wherein, R ¹ is a C ₁ -C ₆ alkyl group (the alkyl group may be substituted with the same or different 1 to 5 halogen atoms), a C ₂ -C ₆ alkenyl group (the The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C ₂
-C ₆ alkynyl group, phenyl group ｛The phenyl group is
1 to 5 identical or different halogen atoms, C ₁
A C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is the same or different 1 to 5 halogen atoms) May be substituted with 5 halogen atoms) or a cyano group. {Or 5- or 6-membered heterocyclic group} The heterocyclic group contains at least one nitrogen atom, oxygen atom or sulfur atom and is the same or different from 1 to 3
Halogen atoms, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is Same or different 1 to 5
May be substituted by halogen atoms. ) Or a cyano group. ｝, And n is
0, 1 or 2; R ² and R ³ are the same or different and each represent a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halogen atom or a cyano group, or
R ² and R ³ are taken together with the carbon atoms to which they are bonded to form a C ₃ -C ₇ cycloalkyl group, wherein the cycloalkyl group is the same or different and has 1 to 5 C ₁ -C ₆ alkyl groups ( The alkyl group may be substituted with the same or different 1 to 5 halogen atoms.), C
₂ -C ₆ alkenyl group (said alkenyl group is the same or different 1 to 3 halogen atoms may be substituted.), C ₁ -C ₆ alkoxy group (said alkoxy group has the same or different 1 Or 5 or more halogen atoms.) Or a halogen atom. Wherein A is an oxygen atom, a sulfur atom or a group of the formula NR ⁶ , wherein R is
⁶ is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), C _2-
A C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ alkoxy group (the alkoxy group may be substituted by the same or different 1 to 5 halogen atoms), C ₂ -C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₆ alkylthio group (the alkylthio group may be substituted by the same or different 1 to 5 halogen atoms), phenyl group, It represents a phenoxy group, a phenylthio group, a formyl group, a C ₂ -C ₆ alkylcarbonyl group, a nitro group or a cyano group. Represents p, p represents 0, 1 or 2, Y represents a halogen atom, a C ₁ -C ₆ alkyl group (the alkyl group is the same or different and is substituted by 1 to 5 halogen atoms, good.), C ₂ ~C ₆ alkenyl, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group (said alkoxy group may be substituted by same or different 1 to 5 halogen atoms .), C ₂ ~C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₆ alkylthio group (said alkylthio group may be substituted by same or different 1 to 5 halogen atoms Good)), a phenyl group, a phenoxy group, a phenylthio group,
Formyl, C ₂ -C ₆ alkylcarbonyl group, a nitro group or a cyano group, when p is 2, each of the plurality of Y may be the same or different, R ⁴ and R ⁵ are the same or different, Hydrogen atom, C ₁ -C ₆ alkyl group (the alkyl group may be the same or different 1 to 5 halogen atoms or one C ₁ -C ₆ alkoxy group, C ₁ -C ₆
It may be substituted by an alkylthio group, a C ₂ -C ₇ alkoxycarbonyl group, a pyridyloxy group, a cyano group or a hydroxyl group. ), C ₂ -C ₆ alkenyl group (said alkenyl group may be substituted by 1 to 3 identical or different halogen atoms.), C ₂ ~C ₆ alkynyl group, a formyl group, C ₂ -C ₁₀ alkylcarbonyl groups ｛The alkylcarbonyl groups may be the same or different 1 to 5 halogen atoms or one C ₁ -C ₆ alkoxy group, phenoxy group (the phenoxy group may be the same or different 1 to 5 C ₁ -C ₆ alkyl group, C ₁ -C ₆
It may be substituted by an alkoxy group or a halogen atom. ), A C ₁ -C ₆ alkylthio group, a phenylthio group (the phenylthio group is substituted with _{1 to} 5 identical or different C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. good.), a carboxyl group, may be substituted by C ₂ -C ₇ alkoxycarbonyl group or a cyano group. ｝, C ₃ -C ₇ alkenylcarbonyl group (the alkenylcarbonyl group may be substituted by the same or different 1 to 5 halogen atoms or 1 phenyl group or C ₂ -C ₇ alkoxycarbonyl group. ), C ₃ -C ₇ alkynylcarbonyl group, benzoyl group (the benzoyl group may be the same or different 1 to 5 halogen atoms or C ₁ -C ₆
Alkyl group or one carboxyl group or C ₂ -C ₇
It may be substituted by an alkoxycarbonyl group. ), A pyridylcarbonyl group (the pyridylcarbonyl group may be substituted by the same or different 1 to 4 halogen atoms or a C _{1 to} C ₆ alkyl group), a thienylcarbonyl group (the thienylcarbonyl group is May be substituted by the same or different 1 to 3 halogen atoms or C ₁ -C ₆ alkyl groups), C ₂ -C ₇ alkyl (thiocarbonyl) group {-C
(= S)-{, phenyl (thiocarbonyl) group} -C
(= S)-｝, C ₂ -C ₇ alkoxycarbonyl group (the alkoxycarbonyl group may be the same or different 1 to 5 halogen atoms or one C ₁ -C ₆ alkoxy group, C ₁ -C ₆ the alkylthio group or a cyano group may be substituted.), C ₃ ~C ₇ alkenyloxycarbonyl group, a phenoxycarbonyl group (said phenoxycarbonyl group may be the same or different 1 to 5 halogen atoms or C ₁ -C _6- alkyl group), C ₂ -C ₇ (alkylthio) carbonyl group ｛-
S—C (＝ O)-｝, (phenylthio) carbonyl group,
C ₂ -C ₇ alkyl dithio group, a phenyl dithio group, C ₃ -C ₈ alkylcarbonyl group, phenylcarbonyl group, C ₃ -C ₈ alkoxycarbonyl group, a phenoxycarbonyl group, an amino group {said The aminocarbonyl group may be the same or different one or two C ₁ -C ₆ alkyl groups, C ₂ -C ₇ alkoxycarbonyl groups, (C ₂ -C ₆
C ₇ alkoxycarbonyl) C ₁ -C ₆ alkyl group or a
Phenyl groups (the phenyl groups may be substituted with the same or different 1 to 5 halogen atoms). ｝, An aminothiocarbonyl group (the aminothiocarbonyl group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups), a furanylcarbonyl group (the furanylcarbonyl group is may be substituted by 1 to 3 identical or different halogen atoms.), pyrazolyl group (the pyrazolyl group may be the same or different 1 or 2 C ₁ -C ₆ alkyl group or a halogen atom May be substituted.), C _1-
C ₆ alkylsulfonyl group, phenylsulfonyl group (the phenylsulfonyl group may be substituted by the same or different 1 to 5 C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. ) Or an aminosulfonyl group (the aminosulfonyl group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups), or R ⁴ and R ⁵ together And a methylidene group {the methylidene group may be the same or different and one or two C ₁ -C ₆ alkyl groups (the alkyl group may be substituted with the same or different 1 to 5 halogen atoms. ), phenyl group (said phenyl group are the same or are selected from the group consisting of C ₁ -C ₆ alkyl group, a halogen atom and C ₁ -C ₆ alkoxy group By 1 to 5 substituents which became may be substituted.), A halogen atom, C ₂ -C ₇ alkoxycarbonyl group, phenoxycarbonyl group or amino group {said amino group may be the same or different 1 or 2 C ₁
-C ₆ alkyl group or (C ₁ -C ₆ alkoxy) C ₁ -C ₆
It may be substituted by an alkyl group. ｝ May be substituted. Or R ⁴ and R ⁵ together with the nitrogen atom to which they are attached form succinimide, phthalimide or pyrrole-2,5-dione;
Halogen atom, C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), C ₁ -C ₆ alkoxy group (the alkoxy group is the same Or different 1 to 5
May be substituted by halogen atoms. ), C ₂
-C ₇ alkoxycarbonyl group or (C ₁ -C ₆ alkyl) aminocarbonyl group (said alkylaminocarbonyl group, the same or different 1 to 5 halogen atoms may be substituted.) Indicates, m is 1,
2, 3, 4 or 5 is indicated. ] The heteroaryl hydrazone compound represented by these, or its salt. 2. R ¹ is a C ₁ -C ₄ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 fluorine or chlorine atoms) or C ₂ -C ₄ alkyl group.
The heteroaryl hydrazone compound according to claim 1, which is a C ₄ alkenyl group, or a salt thereof. 3. The heteroarylhydrazone compound or a salt thereof according to claim ₁ , wherein R ¹ is a C ₁ -C ₃ alkyl group. 4. The heteroarylhydrazone compound or a salt thereof according to claim 1, wherein n is 0 or 2. 5. The method according to claim 1, wherein R ² and R ³ are the same or different and each is a hydrogen atom or a C ₁ -C ₄ alkyl group.
Or the salt thereof. 6. The heteroarylhydrazone compound according to claim 1, wherein R ² and R ³ are both hydrogen atoms, or a salt thereof. 7. A is an oxygen atom, a sulfur atom or a compound of the formula NR ⁶
In the formula, R ⁶ represents a hydrogen atom or a C ₁ -C ₄ alkyl group. The heteroarylhydrazone compound or a salt thereof according to any one of claims 1 to 6, wherein 8. The heteroarylhydrazone compound according to claim 1, wherein A is an oxygen atom or a sulfur atom, or a salt thereof. 9. The heteroarylhydrazone compound according to claim 1, wherein A is a sulfur atom, or a salt thereof. 10. The heteroarylhydrazone compound or a salt thereof according to claim 1, wherein p is 0. 11. R ⁴ and R ⁵ are the same or different,
A hydrogen atom, a C ₁ -C ₄ alkyl group (the alkyl group may be the same or different 1 to 5 fluorine or chlorine atoms or one C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio group, C ₂ -C ₅ alkoxycarbonyl group, pyridyloxy group, may be substituted by a cyano group or a hydroxyl group.), C ₂ ~C ₄ alkenyl group, C ₂ -C ₄ alkynyl group, C ₂ -C ₁₀ alkylcarbonyl group (The alkylcarbonyl group is the same or different from one to five fluorine or chlorine atoms or one C ₁ -C ₄ alkoxy group, phenoxy group, C ₁ -C ₄ alkylthio group, phenylthio group or cyano group. may be substituted.), C ₃ -C ₅ alkenyl group (the alkenyl group may be the same or different 1 to 5 substituents fluoride The atom or chlorine atom, or one phenyl group may be substituted.), C ₃ -C ₅ alkynyl group, a benzoyl group (the benzoyl group, which may be the same or different 1 to 5 fluorine atoms, chlorine atoms or by a bromine atom or a C ₁ -C ₄ alkyl group may be substituted.), pyridylcarbonyl group, thienylcarbonyl group, C ₂ -C ₅ alkyl (thiocarbonyl) group {-C
(= S)-{, phenyl (thiocarbonyl) group} -C
(= S)-｝, a C ₂ -C ₅ alkoxycarbonyl group (the alkoxycarbonyl group may be the same or different from 1 to 5 fluorine or chlorine atoms or 1 C ₁ to
It may be substituted by a C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group or a cyano group. ), C ₃ -C ₅ alkenyloxycarbonyl group, a phenoxycarbonyl groups, C
₂ -C ₅ (alkylthio) carbonyl group {-S-C (=
O) -}, (phenylthio) carbonyl group, C ₂ -C ₅ alkyl dithio group, a phenyl dithio group, C ₃ -C ₆ alkylcarbonyl group, a phenylcarbonyl group, C ₃ -C ₆ alkoxycarbonyl group A phenoxycarbonylcarbonyl group, an aminocarbonyl group ｛the aminocarbonyl group is
1 or 2 identical or different C ₁ -C ₄ alkyl groups or 1 phenyl group (the phenyl group is substituted by 1 to 5 identical or different fluorine, chlorine or bromine atoms. May be substituted. ｝, An aminothiocarbonyl group (the aminothiocarbonyl group may be substituted by the same or different one or two C ₁ -C ₄ alkyl groups),
C ₁ -C ₄ alkylsulfonyl group, phenylsulfonyl group (the phenylsulfonyl group may be substituted by the same or different 1 to 5 C ₁ -C ₄ alkyl groups, fluorine atom, chlorine atom or bromine atom. .) or aminosulfonyl group (the aminosulfonyl group is the same or different one or two C ₁ -C ₄ alkyl group may be substituted.) indicates, or, R ⁴ and R ⁵ together Wherein the methylidene group is the same or different one or two C ₁ -C ₄ alkyl groups (the alkyl groups are substituted by the same or different 1 to 5 fluorine or chlorine atoms; A phenyl group (the phenyl group is selected from the group consisting of a C ₁ -C ₄ alkyl group, a halogen atom and a C ₁ -C ₄ alkoxy group). May be substituted with one or different 1 to 5 substituents), a C ₂ -C ₅ alkoxycarbonyl group, a phenoxycarbonyl group or an amino group (the amino group may be the same or different 1 or 2 the C ₁ -C ₄ alkyl group may be substituted.) it may be substituted with. The heteroarylhydrazone compound or a salt thereof according to any one of claims 1 to 10, wherein 12. R ⁴ and R ⁵ are the same or different,
Hydrogen atom, C ₁ -C ₂ alkyl group (the alkyl group is 1
It may be substituted by C ₁ -C ₂ alkoxy groups, C ₁ -C ₂ alkylthio groups or C ₂ -C ₃ alkoxycarbonyl groups. ), A C ₂ -C ₁₀ alkylcarbonyl group (the alkylcarbonyl group may be the same or different from 1 to 3
It may be substituted by one fluorine atom or chlorine atom or one C ₁ -C ₂ alkoxy group, phenoxy group, C ₁ -C ₂ alkylthio group or cyano group. ), C ₃ ~
A C ₄ alkenylcarbonyl group, a benzoyl group (the benzoyl group may be substituted by the same or different 1 to 5 fluorine or chlorine atoms),
Pyridylcarbonyl group, thienylcarbonyl group, C _2-
C ₅ alkoxycarbonyl group (the alkoxy group may be substituted by same or different 1 to 5 fluorine atoms or chlorine atoms or one C ₁ -C ₂ alkoxy group.), C ₃ -C ₄ alkenyloxycarbonyl group, C ₃ -C ₄ alkoxycarbonylcarbonyl group, aminocarbonyl group The aminocarbonyl group may be the same or different 1 or 2 C ₁ -C ₂ alkyl groups or 1 phenyl group (such as The phenyl group may be substituted by one fluorine atom or chlorine atom.). ｝, An aminothiocarbonyl group (the aminothiocarbonyl group is one C ₁
~C may be substituted by ₂ alkyl groups. ) Or C ₁
~ C ₂ alkylsulfonyl group, or R ⁴ and R ⁵
Together form a methylidene group ｛
The same or different one or two C ₁ -C ₂ alkyl groups, C ₂ -C ₃ alkoxycarbonyl groups or amino groups (the amino group is the same or different one or two C ₁ -C ₂
~C may be substituted by ₂ alkyl groups. ). The heteroarylhydrazone compound or a salt thereof according to any one of claims 1 to 10, wherein 13. R ⁴ and R ⁵ are the same or different,
Hydrogen atom, methyl group (the methyl group may be substituted by one ethoxy group or ethoxycarbonyl group), C ₂ -C ₁₀ alkylcarbonyl group (the alkylcarbonyl group may be the same or different 1 to It may be substituted by three chlorine atoms or one methoxy group, phenoxy group, methylthio group or cyano group), propenylcarbonyl group, benzoyl group (the benzoyl group may be the same or different 1 to 5 A pyridylcarbonyl group, a thienylcarbonyl group, a C ₂ -C ₅ alkoxycarbonyl group (the alkoxycarbonyl group may be the same or different from one to three chlorine atoms or one methoxy group) An allyloxycarbonyl group, butenyloxy Rubonyl group, ethoxycarbonylcarbonyl group, aminocarbonyl group The aminocarbonyl group is substituted by one methyl group or phenyl group (the phenyl group may be substituted by one chlorine atom). Good. ｝ Represents a monomethylaminothiocarbonyl group or a methanesulfonyl group, or R ⁴ and R ⁵ are taken together to form a methylidene group. ｛The methylidene group is one or two same or different methyl groups, ethoxycarbonyl groups. Or it may be substituted by a monoethylamino group. ｝
Or the salt thereof. 14. The heteroarylhydrazone compound or a salt thereof according to claim 1, wherein X is a chlorine atom, a bromine atom or a fluorine atom, and m is 1. 15. The method according to claim 1, wherein the substitution position of X is 4-position.
5. The heteroarylhydrazone compound or a salt thereof according to 4. 16. An agricultural chemical comprising the heteroarylhydrazone compound or a salt thereof according to any one of claims 1 to 15 as an active ingredient. 17. The following general formula (II):[Wherein, R^TwoAnd R^ThreeAre the same or different
Child, C₁~ C₆Alkyl group, C_Two~ C₆Alkenyl group, halo
A gen atom or a cyano group;^TwoAnd R
^ThreeTogether with these bonding carbon atoms_Three~ C
₇Cycloalkyl group--the cycloalkyl group is the same
Or 1 to 5 different C₁~ C₆Alkyl group
The alkyl group is the same or different 1 to 5 halo
It may be substituted by a gen atom. ), C_Two~ C₆Al
Kenyl group (the alkenyl group may be the same or different
Substituted with 1 to 3 halogen atoms
No. ), C ₁~ C₆An alkoxy group (the alkoxy group is
By 1 to 5 identical or different halogen atoms
It may be substituted. ) Or substituted by a halogen atom
You may be. Ａ may be formed, where A is an oxygen atom,
Yellow atom or formula NR⁶In the formula, R represents⁶Is hydrogen
Atom, halogen atom, C₁~ C₆Alkyl group (the alkyl
1 to 5 halogen atoms which are the same or different
May be replaced by a child. ), C_Two~ C₆Alkenyl
Group, C_Two~ C₆Alkynyl group, C₁~ C₆Alkoxy group (this
The alkoxy group is the same or different from 1 to 5
It may be substituted by a halogen atom. ), C_Two~ C₆
Alkenyloxy group, C_Two~ C₆Alkynyloxy group, C
₁~ C₆An alkylthio group (the alkylthio group is the same
Or 1 to 5 different halogen atoms
You may be. ), Phenyl, phenoxy, phenyl
Luthio group, formyl group, C_Two~ C₆Alkylcarbonyl
Group, nitro group or cyano group. ｝, And p is
0, 1 or 2; Y is a halogen atom, C₁~ C₆A
Alkyl group (the alkyl group is the same or different
From 5 to 5 halogen atoms
No. ), C_Two~ C₆Alkenyl group, C_Two~ C₆Alkynyl
Group, C₁~ C₆An alkoxy group (the alkoxy group is the same
Or substituted by 1 to 5 different halogen atoms
May have been. ), C_Two~ C₆Alkenyloxy group, C
_Two~ C₆Alkynyloxy group, C₁~ C₆Alkylthio group
(The alkylthio groups may be the same or different
It may be substituted by 5 halogen atoms. ),
Phenyl, phenoxy, phenylthio, formyl
Group, C_Two~ C₆Alkylcarbonyl group, nitro group or shea
A plurality of Y are the same when p is 2
X may be one or different, and X is a halogen atom, C₁~
C₆Alkyl group (the alkyl group may be the same or different
Substituted with only 1 to 5 halogen atoms
No. ), C₁~ C₆An alkoxy group (the alkoxy group is
By 1 to 5 identical or different halogen atoms
It may be substituted. ), C_Two~ C₇Alkoxycarboni
Or (C₁~ C₆Alkyl) aminocarbonyl group (this
The alkylaminocarbonyl groups are the same or different
From 1 to 5 halogen atoms
No. And m represents 1, 2, 3, 4 or 5;
⁷Is a hydrogen atom, halogen atom, mercapto group, hydroxyl
Group, C_Two~ C₇Alkylcarbonylthio group, C₁~ C₆Al
Killsulfonyloxy group, C₆~ C_TenArylsulfoni
Ruoxy group (the arylsulfonyloxy group is the same
Or 1-5 different Cs₁~ C₆By alkyl group
May be substituted. ), Amidinosulfenyl group or
Is the formula SO_nR¹[Wherein, R¹Is C₁~ C₆Alkyl group (this
The alkyl group is the same or different and has 1 to 5 halo groups.
It may be substituted by a halogen atom. ), C_Two~ C₆A
Alkenyl group (the alkenyl groups may be the same or different
Substituted by one to three halogen atoms
No. ), C_Two~ C₆Alkynyl group, phenyl group
Nyl group is the same or different 1 to 5 halogens
Atom, C₁~ C₆An alkyl group (the alkyl group is the same
Or 1 to 5 different halogen atoms
You may be. ), C₁~ C₆Alkoxy group (the relevant alcohol
The xy group is the same or different 1 to 5 halogens
It may be substituted by an atom. ) Or cyano group
It may be substituted. ｝ Or 5- or 6-membered heterocyclic group
｛The heterocyclic group has at least one nitrogen atom,
Containing the same or different
3 to 3 halogen atoms, C₁~ C₆Alkyl group
The alkyl group is the same or different 1 to 5 halogeno groups.
May be substituted by a substituent atom. ), C₁~ C₆Arco
A xy group (the alkoxy group may be the same or different
And may be substituted with from 5 to 5 halogen atoms. )
Or it may be substituted by a cyano group. ｝, And n
Represents 0, 1 or 2. ] Is shown. ]so
The represented heteroarylcarbonyl compound. 18. A compound represented by the following general formula (III):[Wherein, R^TwoAnd R^ThreeAre the same or different
Child, C₁~ C₆Alkyl group, C_Two~ C₆Alkenyl group, halo
A gen atom or a cyano group;^TwoAnd R
^ThreeTogether with these bonding carbon atoms_Three~ C
₇Cycloalkyl group--the cycloalkyl group is the same
Or 1 to 5 different C₁~ C₆Alkyl group
The alkyl group is the same or different 1 to 5 halo
It may be substituted by a gen atom. ), C_Two~ C₆Al
Kenyl group (the alkenyl group may be the same or different
Substituted with 1 to 3 halogen atoms
No. ), C ₁~ C₆An alkoxy group (the alkoxy group is
By 1 to 5 identical or different halogen atoms
It may be substituted. ) Or substituted by a halogen atom
You may be. Ａ may be formed, where A is an oxygen atom,
Yellow atom or formula NR⁶In the formula, R represents⁶Is hydrogen
Atom, halogen atom, C₁~ C₆Alkyl group (the alkyl
1 to 5 halogen atoms which are the same or different
May be replaced by a child. ), C_Two~ C₆Alkenyl
Group, C_Two~ C₆Alkynyl group, C₁~ C₆Alkoxy group (this
The alkoxy group is the same or different from 1 to 5
It may be substituted by a halogen atom. ), C_Two~ C₆
Alkenyloxy group, C_Two~ C₆Alkynyloxy group, C
₁~ C₆An alkylthio group (the alkylthio group is the same
Or 1 to 5 different halogen atoms
You may be. ), Phenyl, phenoxy, phenyl
Luthio group, formyl group, C_Two~ C₆Alkylcarbonyl
Group, nitro group or cyano group. ｝, And p is
0, 1 or 2; Y is a halogen atom, C₁~ C₆A
Alkyl group (the alkyl group is the same or different
From 5 to 5 halogen atoms
No. ), C_Two~ C₆Alkenyl group, C_Two~ C₆Alkynyl
Group, C₁~ C₆An alkoxy group (the alkoxy group is the same
Or substituted by 1 to 5 different halogen atoms
May have been. ), C_Two~ C₆Alkenyloxy group, C
_Two~ C₆Alkynyloxy group, C₁~ C₆Alkylthio group
(The alkylthio groups may be the same or different
It may be substituted by 5 halogen atoms. ),
Phenyl, phenoxy, phenylthio, formyl
Group, C_Two~ C₆Alkylcarbonyl group, nitro group or shea
A plurality of Y are the same when p is 2
May be one or different;^FourAnd R^FiveAre the same or
Differently, hydrogen atom, C₁~ C₆Alkyl group (the alkyl
1 to 5 halogen atoms which are the same or different
Child or one C₁~ C₆Alkoxy group, C₁~ C₆Alkyl
Thio group, C_Two~ C₇Alkoxycarbonyl group, pyridylo
Substituted by a xy, cyano or hydroxyl group
Good. ), C_Two~ C₆Alkenyl group (the alkenyl group
Represents one or three identical or different halogen atoms.
It may be more substituted. ), C_Two~ C₆Alkynyl group,
Formyl group, C_Two~ C_TenAlkylcarbonyl group
The alkylcarbonyl group may be the same or different from 1 to 5
One halogen atom or one C₁~ C₆Alkoxy group,
Phenoxy groups (the phenoxy groups are the same or different
1 to 5 C₁~ C₆Alkyl group, C₁~ C₆Alkoki
It may be substituted by a silyl group or a halogen atom. ),
C₁~ C₆Alkylthio group, phenylthio group (the phenyl
A luthio group is the same or different from one to five C₁~
C₆Alkyl group, C₁~ C₆Alkoxy group or halogen source
May be replaced by a child. ), Carboxyl group, C
_Two~ C₇By an alkoxycarbonyl group or a cyano group
It may be substituted. ｝, C_Three~ C₇Alkenylcarboni
(The alkenylcarbonyl group may be the same or different
1 to 5 halogen atoms or 1 phenyl group
Or C_Two~ C₇Substituted by an alkoxycarbonyl group
You may be. ), C_Three~ C₇Alkynylcarbonyl group,
Benzoyl group (the benzoyl group may be the same or different
Only 1 to 5 halogen atoms or C₁~ C₆Archi
Or one carboxyl group or C_Two~ C₇Arco
It may be substituted by a xycarbonyl group. ), Pil
A zircarbonyl group (the pyridylcarbonyl group is the same
Or 1 to 4 different halogen atoms or C₁~
C₆It may be substituted by an alkyl group. ), Thieni
Carbonyl group (the thienylcarbonyl group is the same
1 to 3 different halogen atoms or C₁~ C₆
It may be substituted by an alkyl group. ), C_Two~ C₇A
Alkyl (thiocarbonyl) group {-C (= S)-},
Nyl (thiocarbonyl) group {-C (= S)-}, C_Two~
C₇Alkoxycarbonyl group (the alkoxycarbon
1 to 5 halogen atoms which are the same or different
Child or one C₁~ C₆Alkoxy group, C₁~ C₆Alkyl
Substituted by a thio or cyano group
No. ), C_Three~ C₇Alkenyloxycarbonyl group,
A nonoxycarbonyl group (the phenoxycarbonyl group is
1 to 5 identical or different halogen atoms or C
₁~ C₆It may be substituted by an alkyl group. ), C_Two
~ C₇(Alkylthio) carbonyl group ｛-SC (=
O)-｝, (phenylthio) carbonyl group, C_Two~ C₇A
Ruquildithiocarbonyl group, phenyldithiocarbonyl
Group, C_Three~ C₈Alkylcarbonylcarbonyl group, phenyl
Carbonyl group, C_Three~ C₈Alkoxycarbo
Nilcarbonyl group, phenoxycarbonylcarbonyl
Group, aminocarbonyl group ｛The aminocarbonyl group is
1 or 2 identical or different C₁~ C₆Alkyl
Group, C_Two~ C₇An alkoxycarbonyl group, (C_Two~ C₇Al
Coxycarbonyl) C₁~ C₆An alkyl group or one
A phenyl group (the phenyl group may be the same or different
It may be substituted by up to 5 halogen atoms. )
It may be more substituted. ｝, Aminothiocarbonyl group
(The aminothiocarbonyl groups may be the same or different
One or two C₁~ C₆Substituted by an alkyl group
May be. ), Furanylcarbonyl group (the furanyl carb
The bonyl group is the same or different one to three halogen
May be substituted by a substituent atom. ), Pyrazolylcal
A bonyl group (the pyrazolylcarbonyl group is the same
Is one or two different C₁~ C₆Alkyl group or halogen
May be substituted by a substituent atom. ), C₁~ C₆Archi
Rusulfonyl group, phenylsulfonyl group (the phenyl
Sulfonyl groups may be the same or different from one to five C
₁~ C₆Alkyl group, C₁~ C₆Alkoxy group or halogen
It may be substituted by an atom. ) Or aminosulfoni
(The aminosulfonyl groups may be the same or different
One or two C₁~ C₆Substituted by an alkyl group
May be. ) Or R^FourAnd R^FiveTogether
A methylidene group--the methylidene groups may be the same or different
Only one or two Cs₁~ C₆Alkyl group (the alkyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ), A phenyl group (the phenyl
The radical is C₁~ C₆Alkyl group, halogen atom and C₁~
C₆Identical or selected from the group consisting of alkoxy groups
Substituted with 1 to 5 different substituents.
No. ), Halogen atom, C_Two~ C₇Alkoxycarbonyl
Group, phenoxycarbonyl group or amino group
The groups are the same or different and one or two C₁~ C₆Al
A kill group or (C₁~ C₆Alkoxy) C₁~ C₆Alkyl group
May be substituted by Has been replaced by｝
No. ｝ Or R^FourAnd R^FiveBut they are combined
With succinimide, phthalimide or
X forms a pyrrole-2,5-dione;
Child, C₁~ C₆An alkyl group (the alkyl group may be the same or different
Or substituted by 1 to 5 different halogen atoms
May be. ), C₁~ C₆Alkoxy group (the alkoxy
The groups are 1 to 5 halogen atoms, the same or different.
May be replaced by a child. ), C_Two~ C₇Alkoxy
Carbonyl group or (C₁~ C₆Alkyl) aminocarboni
(The alkylaminocarbonyl group is the same or different
Is substituted by 1 to 5 different halogen atoms
May be. ) And m represents 1, 2, 3, 4 or 5.
Then R^7aRepresents a hydrogen atom, a halogen atom, a mercapto group,
Hydroxyl group, C_Two~ C₇Alkylcarbonylthio group, C₁~ C₆
Alkylsulfonyloxy group, C₆~ C_TenArylsul
A honyloxy group (the arylsulfonyloxy group is
1 to 5 same or different C₁~ C₆Alkyl group
May be substituted by ) Or amidinosulfeni
Represents a hydroxyl group. And a heteroaryl hydrazone represented by the formula:
Compound. 19. A compound represented by the following general formula (IV):[Wherein, R¹Is C₁~ C₆Alkyl group (the alkyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ), C_Two~ C₆Alkenyl group
(The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C_Two
~ C₆Alkynyl group, phenyl group ｛the phenyl group is
1 to 5 identical or different halogen atoms, C₁
~ C₆An alkyl group (the alkyl groups may be the same or different
Substituted by 1 to 5 halogen atoms
Good. ), C₁~ C₆An alkoxy group (the alkoxy group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ) Or substituted by a cyano group
You may be. {Or 5- or 6-membered heterocyclic group}
A heterocyclic group has at least one nitrogen or oxygen atom.
1 to 3 containing the same or different sulfur atoms
Halogen atoms, C₁~ C₆Alkyl group (the alkyl
The groups are the same or different and are 1 to 5 halogen atoms
May be substituted by ), C₁~ C₆Alkoxy group
(The alkoxy group may be the same or different from 1 to 5
May be substituted by halogen atoms. ) Or shi
It may be substituted by an ano group. ｝, And n is
0, 1 or 2;^TwoAnd R^ThreeAre the same or different
Is a hydrogen atom, C₁~ C₆Alkyl group, C_Two~ C₆Arche
A nyl group, a halogen atom or a cyano group, or
R^TwoAnd R^ThreeTogether with these attached carbon atoms
C_Three~ C₇Cycloalkyl group ｛the cycloalkyl group
Are the same or different 1 to 5 C₁~ C₆Archi
(The alkyl group may be the same or different
It may be substituted by 5 halogen atoms. ), C
_Two~ C₆An alkenyl group (the alkenyl group may be the same or different
Is replaced by one to three different halogen atoms
May be. ), C₁~ C₆An alkoxy group (the alkoxy
The groups are the same or different and are 1 to 5 halogen atoms
May be substituted by ) Or by a halogen atom
It may be substituted. Ａ may be formed, and A is an oxygen source
Atom, sulfur atom or formula NR⁶In the formula, R represents
⁶Is a hydrogen atom, a halogen atom, C₁~ C₆Alkyl group
(1 to 5 identical or different alkyl groups
May be substituted by a halogen atom. ), C_Two~
C₆Alkenyl group, C_Two~ C₆Alkynyl group, C₁~ C₆A
Alkoxy group (the alkoxy groups are the same or different
From 1 to 5 halogen atoms
No. ), C_Two~ C₆Alkenyloxy group, C_Two~ C₆Archi
Nyloxy group, C₁~ C₆Alkylthio group (the alkyl
A thio group is the same or different 1 to 5 halogen
It may be substituted by an atom. ), Phenyl group,
Nonoxy group, phenylthio group, formyl group, C_Two~ C₆Al
It represents a kill carbonyl group, a nitro group or a cyano group. ｝
And p represents 0, 1 or 2, and Y represents a halogen atom.
Child, C₁~ C₆An alkyl group (the alkyl group may be the same or different
Or substituted by 1 to 5 different halogen atoms
May be. ), C_Two~ C₆Alkenyl group, C_Two~ C₆Al
Quinyl group, C₁~ C₆An alkoxy group (the alkoxy group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ), C_Two~ C₆Alkenyloxy
Si group, C_Two~ C₆Alkynyloxy group, C₁~ C₆Alkyl
A thio group (the alkylthio groups may be the same or different
Substituted with 1 to 5 halogen atoms
No. ), Phenyl, phenoxy, phenylthio,
Formyl group, C_Two~ C₆Alkylcarbonyl group, nitro group
Or a cyano group, and when p is 2, a plurality of Y
X may be the same or different.
Child, C₁~ C₆An alkyl group (the alkyl group may be the same or different
Or substituted by 1 to 5 different halogen atoms
May be. ), C₁~ C₆Alkoxy group (the alkoxy
The groups are 1 to 5 halogen atoms, the same or different.
May be replaced by a child. ), C_Two~ C₇Alkoxy
Carbonyl group or (C₁~ C₆Alkyl) aminocarboni
(The alkylaminocarbonyl group is the same or different
Is substituted by 1 to 5 different halogen atoms
May be. ) And m represents 1, 2, 3, 4 or 5.
You. A heteroarylcarbonyl compound represented by the formula:
The following general formula (V)[Wherein, R^FourAnd R^FiveAre the same or different
Child, C₁~ C₆An alkyl group (the alkyl group may be the same or different
Or 1 to 5 different halogen atoms or 1 C₁
~ C₆Alkoxy group, C₁~ C₆Alkylthio group, C_Two~ C
₇Alkoxycarbonyl group, pyridyloxy group, cyano
It may be substituted by a group or a hydroxyl group. ), C_Two
~ C₆An alkenyl group (the alkenyl group may be the same or different
Is replaced by one to three different halogen atoms
May be. ), C_Two~ C₆Alkynyl group, formyl group, C
_Two~ C_TenAlkyl carbonyl group ｛the alkyl carbonyl
1 to 5 halogen atoms which are the same or different
Child or one C₁~ C₆Alkoxy group, phenoxy group (this
The phenoxy group may be the same or different from 1 to 5
C ₁~ C₆Alkyl group, C₁~ C₆Alkoxy group or halogen
May be substituted by a substituent atom. ), C₁~ C₆Archi
Luthio group, phenylthio group (the phenylthio group
1 to 5 different Cs₁~ C₆Alkyl group,
C₁~ C₆Substituted by an alkoxy group or a halogen atom
May be. ), Carboxyl group, C_Two~ C₇Alkoxy
Substituted by a carbonyl group or a cyano group
No. ｝, C_Three~ C₇Alkenylcarbonyl group (the
1 to 5 identical or different carbonyl groups
A halogen atom or one phenyl group or C_Two~ C₇
May be substituted by an alkoxycarbonyl group
No. ), C_Three~ C₇Alkynylcarbonyl group, benzoyl
Groups (the benzoyl groups may be the same or different
5 halogen atoms or C₁~ C₆Alkyl group or 1
Carboxyl groups or C_Two~ C₇Alkoxycarbo
It may be substituted by a nyl group. ), Pyridylcarbo
Nyl group (the pyridylcarbonyl group may be the same or different
1 to 4 halogen atoms or C₁~ C₆Alkyl
May be substituted by a group. ), Thienylcarbonyl
Groups (the thienylcarbonyl groups are the same or different
1 to 3 halogen atoms or C₁~ C₆To the alkyl group
It may be more substituted. ), C_Two~ C₇Alkyl (thio
Carbonyl) group {-C (= S)-}, phenyl (thioca
Rubonyl) group {-C (= S)-}, C_Two~ C₇Alkoxy
A carbonyl group (the same alkoxycarbonyl group
Or different 1 to 5 halogen atoms or 1 C
₁~ C₆Alkoxy group, C₁~ C₆Alkylthio group or
It may be substituted by a cyano group. ), C_Three~ C₇Al
Kenyloxycarbonyl group, phenoxycarbonyl group
(The phenoxycarbonyl groups may be the same or different.
1 to 5 halogen atoms or C₁~ C₆To the alkyl group
It may be more substituted. ), C_Two~ C₇(Alkyl
E) carbonyl group {-SC (= O)-}, (phenyl
Thio) carbonyl group, C_Two~ C₇Alkyl dithiocarboni
Group, phenyldithiocarbonyl group, C _Three~ C₈Alkyl
Carbonylcarbonyl group, phenylcarbonylcarboni
Group, C _Three~ C₈Alkoxycarbonylcarbonyl group,
Phenoxycarbonylcarbonyl group, aminocarbonyl group
{The aminocarbonyl groups are the same or different.
Or two C₁~ C₆Alkyl group, C_Two~ C₇Alkoxyka
Rubonyl group, (C_Two~ C₇Alkoxycarbonyl) C₁~
C₆An alkyl group or one phenyl group (the phenyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. )
No. ｝, Aminothiocarbonyl group (the aminothiocar
A bonyl group may be one or two identical or different C₁~
C₆It may be substituted by an alkyl group. ), Fulani
Carbonyl group (the furanylcarbonyl group is the same
Or 1 to 3 different halogen atoms
You may be. ), Pyrazolylcarbonyl group (
The zolylcarbonyl group may be the same or different 1 or 2
C₁~ C₆Substituted by an alkyl group or a halogen atom
You may be. ), C₁~ C₆Alkylsulfonyl group,
Phenylsulfonyl group (the phenylsulfonyl group is
1 to 5 different Cs₁~ C₆Alkyl group,
C₁~ C₆Substituted by an alkoxy group or a halogen atom
May be. ) Or aminosulfonyl group (the aminos
The rufonyl group may be the same or different and one or two C₁
~ C₆It may be substituted by an alkyl group. )
Or R^FourAnd R^FiveTogether form a methylidene group
｛The methylidene group is the same or different 1 or 2
C₁~ C₆An alkyl group (the alkyl group may be the same or different
Or substituted by 1 to 5 different halogen atoms
May be. ), A phenyl group (the phenyl group is a C₁
~ C₆Alkyl group, halogen atom and C₁~ C₆Alkoki
Same or different one selected from the group consisting of
It may be substituted by up to 5 substituents. ), Haloge
Atom, C_Two~ C₇Alkoxycarbonyl group, phenoxy
Carbonyl group or amino group
Or one or two different C₁~ C₆Alkyl group or (C
₁~ C₆Alkoxy) C₁~ C₆Substituted by an alkyl group
May be. ｝ May be substituted. ｝,
Or R^FourAnd R^FiveTogether with the nitrogen atom to which they are attached
Succinimide, phthalimide or pyrrole-2,
Form 5-dione. A hydrazine compound represented by the formula:
With the following general formula (I):[Wherein, R¹, R^Two, R^Three, R^Four, R^Five, N, p, A, Y,
X and m are as defined above. Hetero represented by
A method for producing an arylhydrazone compound. 20. The following general formula (IIIb):[Wherein, R^TwoAnd R^ThreeAre the same or different
Child, C₁~ C₆Alkyl group, C_Two~ C₆Alkenyl group, halo
A gen atom or a cyano group;^TwoAnd R
^ThreeTogether with these bonding carbon atoms_Three~ C
₇Cycloalkyl group--the cycloalkyl group is the same
Or 1 to 5 different C₁~ C₆Alkyl group
The alkyl group is the same or different 1 to 5 halo
It may be substituted by a gen atom. ), C_Two~ C₆Al
Kenyl group (the alkenyl group may be the same or different
Substituted with 1 to 3 halogen atoms
No. ), C ₁~ C₆An alkoxy group (the alkoxy group is
By 1 to 5 identical or different halogen atoms
It may be substituted. ) Or substituted by a halogen atom
You may be. Ａ may be formed, where A is an oxygen atom,
Yellow atom or formula NR⁶In the formula, R represents⁶Is hydrogen
Atom, halogen atom, C₁~ C₆Alkyl group (the alkyl
1 to 5 halogen atoms which are the same or different
May be replaced by a child. ), C_Two~ C₆Alkenyl
Group, C_Two~ C₆Alkynyl group, C₁~ C₆Alkoxy group (this
The alkoxy group is the same or different from 1 to 5
It may be substituted by a halogen atom. ), C_Two~ C₆
Alkenyloxy group, C_Two~ C₆Alkynyloxy group, C
₁~ C₆An alkylthio group (the alkylthio group is the same
Or 1 to 5 different halogen atoms
You may be. ), Phenyl, phenoxy, phenyl
Luthio group, formyl group, C_Two~ C₆Alkylcarbonyl
Group, nitro group or cyano group. ｝, And p is
0, 1 or 2; Y is a halogen atom, C₁~ C₆A
Alkyl group (the alkyl group is the same or different
From 5 to 5 halogen atoms
No. ), C_Two~ C₆Alkenyl group, C_Two~ C₆Alkynyl
Group, C₁~ C₆An alkoxy group (the alkoxy group is the same
Or substituted by 1 to 5 different halogen atoms
May have been. ), C_Two~ C₆Alkenyloxy group, C
_Two~ C₆Alkynyloxy group, C₁~ C₆Alkylthio group
(The alkylthio groups may be the same or different
It may be substituted by 5 halogen atoms. ),
Phenyl, phenoxy, phenylthio, formyl
Group, C_Two~ C₆Alkylcarbonyl group, nitro group or shea
A plurality of Y are the same when p is 2
May be one or different;^FourAnd R^FiveAre the same or
Differently, hydrogen atom, C₁~ C₆Alkyl group (the alkyl
1 to 5 halogen atoms which are the same or different
Child or one C₁~ C₆Alkoxy group, C₁~ C₆Alkyl
Thio group, C_Two~ C₇Alkoxycarbonyl group, pyridylo
Substituted by a xy, cyano or hydroxyl group
Good. ), C_Two~ C₆Alkenyl group (the alkenyl group
Represents one or three identical or different halogen atoms.
It may be more substituted. ), C_Two~ C₆Alkynyl group,
Formyl group, C_Two~ C_TenAlkylcarbonyl group
The alkylcarbonyl group may be the same or different from 1 to 5
One halogen atom or one C₁~ C₆Alkoxy group,
Phenoxy groups (the phenoxy groups are the same or different
1 to 5 C₁~ C₆Alkyl group, C₁~ C₆Alkoki
It may be substituted by a silyl group or a halogen atom. ),
C₁~ C₆Alkylthio group, phenylthio group (the phenyl
A luthio group is the same or different from one to five C₁~
C₆Alkyl group, C₁~ C₆Alkoxy group or halogen source
May be replaced by a child. ), Carboxyl group, C
_Two~ C₇By an alkoxycarbonyl group or a cyano group
It may be substituted. ｝, C_Three~ C₇Alkenylcarboni
(The alkenylcarbonyl group may be the same or different
1 to 5 halogen atoms or 1 phenyl group
Or C_Two~ C₇Substituted by an alkoxycarbonyl group
You may be. ), C_Three~ C₇Alkynylcarbonyl group,
Benzoyl group (the benzoyl group may be the same or different
Only 1 to 5 halogen atoms or C₁~ C₆Archi
Or one carboxyl group or C_Two~ C₇Arco
It may be substituted by a xycarbonyl group. ), Pil
A zircarbonyl group (the pyridylcarbonyl group is the same
Or 1 to 4 different halogen atoms or C₁~
C₆It may be substituted by an alkyl group. ), Thieni
Carbonyl group (the thienylcarbonyl group is the same
1 to 3 different halogen atoms or C₁~ C₆
It may be substituted by an alkyl group. ), C_Two~ C₇A
Alkyl (thiocarbonyl) group {-C (= S)-},
Nyl (thiocarbonyl) group {-C (= S)-}, C_Two~
C₇Alkoxycarbonyl group (the alkoxycarbon
1 to 5 halogen atoms which are the same or different
Child or one C₁~ C₆Alkoxy group, C₁~ C₆Alkyl
Substituted by a thio or cyano group
No. ), C_Three~ C₇Alkenyloxycarbonyl group,
A nonoxycarbonyl group (the phenoxycarbonyl group is
1 to 5 identical or different halogen atoms or C
₁~ C₆It may be substituted by an alkyl group. ), C_Two
~ C₇(Alkylthio) carbonyl group ｛-SC (=
O)-｝, (phenylthio) carbonyl group, C_Two~ C₇A
Ruquildithiocarbonyl group, phenyldithiocarbonyl
Group, C_Three~ C₈Alkylcarbonylcarbonyl group, phenyl
Carbonyl group, C_Three~ C₈Alkoxycarbo
Nilcarbonyl group, phenoxycarbonylcarbonyl
Group, aminocarbonyl group ｛The aminocarbonyl group is
1 or 2 identical or different C₁~ C₆Alkyl
Group, C_Two~ C₇An alkoxycarbonyl group, (C_Two~ C₇Al
Coxycarbonyl) C₁~ C₆An alkyl group or one
A phenyl group (the phenyl group may be the same or different
It may be substituted by up to 5 halogen atoms. )
It may be more substituted. ｝, Aminothiocarbonyl group
(The aminothiocarbonyl groups may be the same or different
One or two C₁~ C₆Substituted by an alkyl group
May be. ), Furanylcarbonyl group (the furanyl carb
The bonyl group is the same or different one to three halogen
May be substituted by a substituent atom. ), Pyrazolylcal
A bonyl group (the pyrazolylcarbonyl group is the same
Is one or two different C₁~ C₆Alkyl group or halogen
May be substituted by a substituent atom. ), C₁~ C₆Archi
Rusulfonyl group, phenylsulfonyl group (the phenyl
Sulfonyl groups may be the same or different from one to five C
₁~ C₆Alkyl group, C₁~ C₆Alkoxy group or halogen
It may be substituted by an atom. ) Or aminosulfoni
(The aminosulfonyl groups may be the same or different
One or two C₁~ C₆Substituted by an alkyl group
May be. ) Or R^FourAnd R^FiveTogether
A methylidene group--the methylidene groups may be the same or different
Only one or two Cs₁~ C₆Alkyl group (the alkyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ), A phenyl group (the phenyl
The radical is C₁~ C₆Alkyl group, halogen atom and C₁~
C₆Identical or selected from the group consisting of alkoxy groups
Substituted with 1 to 5 different substituents.
No. ), Halogen atom, C_Two~ C₇Alkoxycarbonyl
Group, phenoxycarbonyl group or amino group
The groups are the same or different and one or two C₁~ C₆Al
A kill group or (C₁~ C₆Alkoxy) C₁~ C₆Alkyl group
May be substituted by Has been replaced by｝
No. ｝ Or R^FourAnd R^FiveBut they are combined
With succinimide, phthalimide or
Forming pyrrole-2,5-dione, m is 1,2,
Represents 3, 4 or 5, wherein X is a halogen atom, C₁~ C₆A
Alkyl group (the alkyl group is the same or different
From 5 to 5 halogen atoms
No. ), C₁~ C₆An alkoxy group (the alkoxy group is
By 1 to 5 identical or different halogen atoms
It may be substituted. ), C_Two~ C₇Alkoxycarboni
Or (C₁~ C₆Alkyl) aminocarbonyl group (this
The alkylaminocarbonyl groups are the same or different
From 1 to 5 halogen atoms
No. ) And R^7bIs a halogen atom, a mercapto group,
Hydroxyl group, C_Two~ C₇Alkylcarbonylthio group, C₁~ C₆
Alkylsulfonyloxy group, C₆~ C_TenArylsul
A honyloxy group (the arylsulfonyloxy group is
1 to 5 same or different C₁~ C₆Alkyl group
May be substituted by ) Or amidinosulfeni
Represents a hydroxyl group. And a heteroaryl hydrazone represented by the formula:
And a compound represented by the following general formula (VI):[Wherein, R¹Is C₁~ C₆Alkyl group (the alkyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ), C_Two~ C₆Alkenyl group
(The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C_Two
~ C₆Alkynyl group, phenyl group ｛the phenyl group is
1 to 5 identical or different halogen atoms, C₁
~ C₆An alkyl group (the alkyl groups may be the same or different
Substituted by 1 to 5 halogen atoms
Good. ), C₁~ C₆An alkoxy group (the alkoxy group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ) Or substituted by a cyano group
You may be. {Or 5- or 6-membered heterocyclic group}
A heterocyclic group has at least one nitrogen or oxygen atom.
1 to 3 containing the same or different sulfur atoms
Halogen atoms, C₁~ C₆Alkyl group (the alkyl
The groups are the same or different and are 1 to 5 halogen atoms
May be substituted by ), C₁~ C₆Alkoxy group
(The alkoxy group may be the same or different from 1 to 5
May be substituted by halogen atoms. ) Or shi
It may be substituted by an ano group. ｝ And R^7bBut,
Mercapto group, C_Two~ C₇An alkylcarbonylthio group or
When it is an amidinosulfenyl group, Z is a halogen atom
Child, C₁~ C₆Alkylsulfonyloxy group or C₆~ C
_TenArylsulfonyloxy group (the arylsulfonyl group
A ruoxy group is the same or different from one to five C₁
~ C₆It may be substituted by an alkyl group. )
Then R^7bIs a halogen atom, C₁~ C₆Alkylsulfoni
Roxy group or C₆~ C_TenArylsulfonyloxy group
(The arylsulfonyloxy groups are the same or different.
1 to 5 C₁~ C₆Substituted by an alkyl group
May be. ), Z is represented by the formula -SO_qM (expression
In the formula, q represents 0 or 2, and M represents an alkali metal.
You. ) Represents a group represented by^7bIs a hydroxyl group
Where Z is the formula -SSR¹(Where R¹Has the same significance as above.
Show. ). ] The compound represented by
The following general formula (I)[Wherein, R¹, R^Two, R^Three, R^Four, R^Five, N, p, A, Y,
X and m are as defined above. Heteroa represented by
A method for producing a reel hydrazone compound. 21. The following general formula (VII):[Wherein, R¹Is C₁~ C₆Alkyl group (the alkyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ), C_Two~ C₆Alkenyl group
(The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C_Two
~ C₆Alkynyl group, phenyl group ｛the phenyl group is
1 to 5 identical or different halogen atoms, C₁
~ C₆An alkyl group (the alkyl groups may be the same or different
Substituted by 1 to 5 halogen atoms
Good. ), C₁~ C₆An alkoxy group (the alkoxy group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ) Or substituted by a cyano group
You may be. {Or 5- or 6-membered heterocyclic group}
A heterocyclic group has at least one nitrogen or oxygen atom.
1 to 3 containing the same or different sulfur atoms
Halogen atoms, C₁~ C₆Alkyl group (the alkyl
The groups are the same or different and are 1 to 5 halogen atoms
May be substituted by ), C₁~ C₆Alkoxy group
(The alkoxy group may be the same or different from 1 to 5
May be substituted by halogen atoms. ) Or shi
It may be substituted by an ano group. ｝, And n is
0, 1 or 2;^TwoAnd R^ThreeAre the same or different
Is a hydrogen atom, C₁~ C₆Alkyl group, C_Two~ C₆Arche
A nyl group, a halogen atom or a cyano group, or
R^TwoAnd R^ThreeTogether with these attached carbon atoms
C_Three~ C₇Cycloalkyl group ｛the cycloalkyl group
Are the same or different 1 to 5 C₁~ C₆Archi
(The alkyl group may be the same or different
It may be substituted by 5 halogen atoms. ), C
_Two~ C₆An alkenyl group (the alkenyl group may be the same or different
Is replaced by one to three different halogen atoms
May be. ), C₁~ C₆An alkoxy group (the alkoxy
The groups are the same or different and are 1 to 5 halogen atoms
May be substituted by ) Or by a halogen atom
It may be substituted. Ａ may be formed, and A is an oxygen source
Atom, sulfur atom or formula NR⁶In the formula, R represents
⁶Is a hydrogen atom, a halogen atom, C₁~ C₆Alkyl group
(1 to 5 identical or different alkyl groups
May be substituted by a halogen atom. ), C_Two~
C₆Alkenyl group, C_Two~ C₆Alkynyl group, C₁~ C₆A
Alkoxy group (the alkoxy groups are the same or different
From 1 to 5 halogen atoms
No. ), C_Two~ C₆Alkenyloxy group, C_Two~ C₆Archi
Nyloxy group, C₁~ C₆Alkylthio group (the alkyl
A thio group is the same or different 1 to 5 halogen
It may be substituted by an atom. ), Phenyl group,
Nonoxy group, phenylthio group, formyl group, C_Two~ C₆Al
It represents a kill carbonyl group, a nitro group or a cyano group. ｝
And p represents 0, 1 or 2, and Y represents a halogen atom.
Child, C₁~ C₆An alkyl group (the alkyl group may be the same or different
Or substituted by 1 to 5 different halogen atoms
May be. ), C_Two~ C₆Alkenyl group, C_Two~ C₆Al
Quinyl group, C₁~ C₆An alkoxy group (the alkoxy group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. ), C_Two~ C₆Alkenyloxy
Si group, C_Two~ C₆Alkynyloxy group, C₁~ C₆Alkyl
A thio group (the alkylthio groups may be the same or different
Substituted with 1 to 5 halogen atoms
No. ), Phenyl, phenoxy, phenylthio,
Formyl group, C_Two~ C₆Alkylcarbonyl group, nitro group
Or a cyano group, and when p is 2, a plurality of Y
Each may be the same or different;^4aIs a hydrogen atom,
C₁~ C₆Alkyl group (the alkyl group is the same or
1 to 5 different halogen atoms or 1 C₁~ C₆
Alkoxy group, C₁~ C₆Alkylthio group, C_Two~ C₇Al
Oxycarbonyl group, pyridyloxy group, cyano group
Or may be substituted by a hydroxyl group. ), C_Two~ C₆A
Alkenyl group (the alkenyl groups may be the same or different
Substituted by one to three halogen atoms
No. ), C_Two~ C₆Alkynyl group, formyl group, C_Two~ C
_TenAlkylcarbonyl group カ ル ボ ニ ル the alkylcarbonyl group
Are the same or different 1 to 5 halogen atoms or
Is one C₁~ C₆Alkoxy and phenoxy groups
Enoxy groups may be the same or different from one to five C₁
~ C₆Alkyl group, C₁~ C₆Alkoxy group or halogen
It may be substituted by an atom. ), C₁~ C₆Alkyl
Thio group, phenylthio group (the phenylthio group is the same
Or 1-5 different Cs ₁~ C₆Alkyl group, C
₁~ C₆Substituted by an alkoxy group or a halogen atom
May be. ), Carboxyl group, C_Two~ C₇Alkoxyka
May be substituted by a rubonyl group or a cyano group
No. ｝, C_Three~ C₇Alkenylcarbonyl group (the
1 to 5 identical or different carbonyl groups
A halogen atom or one phenyl group or C_Two~ C₇
May be substituted by an alkoxycarbonyl group
No. ), C_Three~ C₇Alkynylcarbonyl group, benzoyl
Groups (the benzoyl groups may be the same or different
5 halogen atoms or C₁~ C₆Alkyl group or 1
Carboxyl groups or C_Two~ C₇Alkoxycarbo
It may be substituted by a nyl group. ), Pyridylcarbo
Nyl group (the pyridylcarbonyl group may be the same or different
1 to 4 halogen atoms or C₁~ C₆Alkyl
May be substituted by a group. ), Thienylcarbonyl
Groups (the thienylcarbonyl groups are the same or different
1 to 3 halogen atoms or C₁~ C₆To the alkyl group
It may be more substituted. ), C_Two~ C₇Alkyl (thio
Carbonyl) group {-C (= S)-}, phenyl (thioca
Rubonyl) group {-C (= S)-}, C_Two~ C₇Alkoxy
A carbonyl group (the same alkoxycarbonyl group
Or different 1 to 5 halogen atoms or 1 C
₁~ C₆Alkoxy group, C₁~ C₆Alkylthio group or
It may be substituted by a cyano group. ), C_Three~ C₇Al
Kenyloxycarbonyl group, phenoxycarbonyl group
(The phenoxycarbonyl groups may be the same or different.
1 to 5 halogen atoms or C₁~ C₆To the alkyl group
It may be more substituted. ), C_Two~ C₇(Alkyl
E) carbonyl group {-SC (= O)-}, (phenyl
Thio) carbonyl group, C_Two~ C₇Alkyl dithiocarboni
Group, phenyldithiocarbonyl group, C_Three~ C₈Alkyl
Carbonylcarbonyl group, phenylcarbonylcarboni
Group, C_Three~ C₈Alkoxycarbonylcarbonyl group,
Phenoxycarbonylcarbonyl group, aminocarbonyl group
{The aminocarbonyl groups are the same or different.
Or two C₁~ C₆Alkyl group, C_Two~ C₇Alkoxyka
Rubonyl group, (C_Two~ C₇Alkoxycarbonyl) C₁~
C₆An alkyl group or one phenyl group (the phenyl group
Represents 1 to 5 identical or different halogen atoms
It may be more substituted. )
No. ｝, Aminothiocarbonyl group (the aminothiocar
A bonyl group may be one or two identical or different C₁~
C₆It may be substituted by an alkyl group. ), Fulani
Carbonyl group (the furanylcarbonyl group is the same
Or 1 to 3 different halogen atoms
You may be. ), Pyrazolylcarbonyl group (
The zolylcarbonyl group may be the same or different 1 or 2
C₁~ C₆Substituted by an alkyl group or a halogen atom
You may be. ), C₁~ C₆Alkylsulfonyl group,
Phenylsulfonyl group (the phenylsulfonyl group is
1 to 5 different Cs₁~ C₆Alkyl group,
C₁~ C₆Substituted by an alkoxy group or a halogen atom
May be. ) Or aminosulfonyl group (the aminos
The rufonyl group may be the same or different and one or two C₁
~ C₆It may be substituted by an alkyl group. )
And X is a halogen atom, C₁~ C₆Alkyl group
The alkyl group is the same or different 1 to 5 halogeno groups.
May be substituted by a substituent atom. ), C₁~ C₆Arco
A xy group (the alkoxy group may be the same or different
From 5 to 5 halogen atoms
No. ), C_Two~ C₇An alkoxycarbonyl group or (C₁~
C₆Alkyl) aminocarbonyl group (the alkylamido group
Nocarbonyl groups are the same or different and 1 to 5
It may be substituted by a halogen atom. ) And m
Represents 1, 2, 3, 4 or 5. Hetero represented by
An arylhydrazone compound represented by the following general formula (VIII):[Wherein, R^5aIs C_Two~ C_TenAlkylcarbonyl group
The alkylcarbonyl groups may be the same or different.
5 halogen atoms or 1 C₁~ C₆Alkoxy
Group, a phenoxy group (the phenoxy group is the same or
1 to 5 different C₁~ C₆Alkyl group, C₁~ C₆A
Substituted with a alkoxy group or a halogen atom
No. ), C₁~ C₆Alkylthio group, phenylthio group (this
The phenylthio groups are the same or different and 1 to 5
C₁~ C₆Alkyl group, C₁~ C₆Alkoxy group or halo
It may be substituted by a gen atom. ), Carboxyl
Group, C_Two~ C₇Alkoxycarbonyl group or cyano group
May be substituted by ｝, C_Three~ C₇Alkenylka
Rubonyl group (the alkenylcarbonyl group may be the same or different
Or 1 to 5 different halogen atoms or 1
Nil group or C_Two~ C₇By an alkoxycarbonyl group
It may be substituted. ), C_Three~ C₇Alkynylcarboni
Group, benzoyl group (the benzoyl group
Is different from 1 to 5 halogen atoms or C₁~ C₆
An alkyl group or one carboxyl group or C_Two~ C₇
May be substituted by an alkoxycarbonyl group
No. ), Pyridylcarbonyl group (the pyridylcarboni
1 to 4 halogen atoms are the same or different.
Child or C₁~ C₆May be substituted by an alkyl group
No. ), Thienylcarbonyl group (the thienyl carbonyl group
1 to 3 halogen atoms are the same or different.
Child or C₁~ C₆May be substituted by an alkyl group
No. ), C_Two~ C₇Alkyl (thiocarbonyl) group ｛-C
(= S)-{, phenyl (thiocarbonyl) group} -C
(= S)-｝, C_Two~ C₇Alkoxycarbonyl group (the
The alkoxycarbonyl groups may be the same or different.
5 halogen atoms or 1 C₁~ C₆Alkoxy
Group, C₁~ C₆Replaced by an alkylthio or cyano group
May be replaced. ), C_Three~ C₇Alkenyloxycal
Bonyl group, phenoxycarbonyl group (the phenoxyca
The rubonyl group is the same or different 1 to 5 halo
Gen atom or C₁~ C₆Substituted by an alkyl group
Good. ), C_Two~ C₇(Alkylthio) carbonyl group
S—C (＝ O)-｝, (phenylthio) carbonyl group,
C_Two~ C₇Alkyldithiocarbonyl group, phenyldithio
Carbonyl group, C_Three~ C₈Alkylcarbonylcarbonyl
Group, phenylcarbonylcarbonyl group, C_Three~ C₈Arco
Xycarbonylcarbonyl group, phenoxycarbonylca
Rubonyl group, aminocarbonyl group
Groups are the same or different and one or two C₁~ C₆A
Alkyl group, C_Two~ C₇An alkoxycarbonyl group, (C_Two~
C₇Alkoxycarbonyl) C₁~ C₆Alkyl group or 1
Phenyl groups (the phenyl groups may be the same or different
Substituted with only 1 to 5 halogen atoms
No. ) May be substituted. ｝, Aminothiocal
A bonyl group (the aminothiocarbonyl group is the same
Is one or two different C₁~ C₆Substituted by alkyl group
May have been. ), Furanylcarbonyl group (the
1 to 3 identical or different carbonyl groups
May be substituted by a halogen atom. ), Pyrazo
A carbonyl group (the pyrazolylcarbonyl group is
One or two different Cs₁~ C₆Alkyl group
May be substituted by a halogen atom. ), C₁~
C₆Alkylsulfonyl group, phenylsulfonyl group
The phenylsulfonyl groups may be the same or different.
5 C₁~ C₆Alkyl group, C₁~ C₆Alkoxy group or
May be substituted by a halogen atom. ) Or Ami
Nosulfonyl group (the same aminosulfonyl group
Or one or two different C₁~ C₆By alkyl group
May be replaced. ) And E is a halogen atom, water
Acid group or formula -OR^5a(Where R^5aHas the same meaning as above.
You. ). ] And the compound represented by
The following general formula (Ia)[Wherein, R¹, R^Two, R^Three, R^4a, R^5a, N, p, A,
Y, X and m are as defined above. Hete represented by]
A method for producing a low aryl hydrazone compound. 22. The following general formula (IX): [Wherein, R ¹ is a C ₁ -C ₆ alkyl group (the alkyl group may be substituted with the same or different 1 to 5 halogen atoms), a C ₂ -C ₆ alkenyl group (the The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C ₂
-C ₆ alkynyl group, phenyl group ｛The phenyl group is
1 to 5 identical or different halogen atoms, C ₁
A C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is the same or different 1 to 5 halogen atoms) May be substituted with 5 halogen atoms) or a cyano group. {Or 5- or 6-membered heterocyclic group} The heterocyclic group contains at least one nitrogen atom, oxygen atom or sulfur atom and is the same or different from 1 to 3
Halogen atoms, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is Same or different 1 to 5
May be substituted by halogen atoms. ) Or a cyano group. ｝, And n is
0, 1 or 2; R ² and R ³ are the same or different and each represent a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halogen atom or a cyano group, or
R ² and R ³ are taken together with the carbon atoms to which they are bonded to form a C ₃ -C ₇ cycloalkyl group, wherein the cycloalkyl group is the same or different and has 1 to 5 C ₁ -C ₆ alkyl groups ( The alkyl group may be substituted with the same or different 1 to 5 halogen atoms.), C
₂ -C ₆ alkenyl group (said alkenyl group is the same or different 1 to 3 halogen atoms may be substituted.), C ₁ -C ₆ alkoxy group (said alkoxy group has the same or different 1 Or 5 or more halogen atoms.) Or a halogen atom. Wherein A is an oxygen atom, a sulfur atom or a group of the formula NR ⁶ , wherein R is
⁶ is a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), C _2-
A C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ alkoxy group (the alkoxy group may be substituted by the same or different 1 to 5 halogen atoms), C ₂ -C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₆ alkylthio group (the alkylthio group may be substituted by the same or different 1 to 5 halogen atoms), phenyl group, It represents a phenoxy group, a phenylthio group, a formyl group, a C ₂ -C ₆ alkylcarbonyl group, a nitro group or a cyano group. Represents p, p represents 0, 1 or 2, Y represents a halogen atom, a C ₁ -C ₆ alkyl group (the alkyl group is the same or different and is substituted by 1 to 5 halogen atoms, good.), C ₂ ~C ₆ alkenyl, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group (said alkoxy group may be substituted by same or different 1 to 5 halogen atoms .), C ₂ ~C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₆ alkylthio group (said alkylthio group may be substituted by same or different 1 to 5 halogen atoms Good)), a phenyl group, a phenoxy group, a phenylthio group,
Formyl, C ₂ -C ₆ alkylcarbonyl group, a nitro group or a cyano group, when p is 2, the plurality of Y may the same or different and each, X is a halogen atom, C ₁ -C ₆ alkyl Group (the alkyl group may be substituted with the same or different 1 to 5 halogen atoms), a C _{1 to} C ₆ alkoxy group (the alkoxy group may be the same or different 1 to 5 halogen atoms) May be substituted by an atom), a C ₂ -C ₇ alkoxycarbonyl group or a (C ₁ -C ₆ alkyl) aminocarbonyl group (the alkylaminocarbonyl group is the same or different from 1 to 5 halogen atoms. And m represents 1, 2, 3, 4, or 5. A heteroarylhydrazone compound represented by the formula:
The following general formula (X) [Wherein, R ⁸ and R ⁹ are the same or different and each represent a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group, a C ₁
-C ₆ alkylthio group, C ₂ -C ₇ alkoxycarbonyl group, phenoxycarbonyl group or amino group (the amino group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups. ), Where R
⁸ and R ⁹ are not simultaneously hydrogen atoms. With a carbonyl compound represented by the following general formula (Ib): [Wherein, R ¹ , R ² , R ³ , R ⁸ , R ⁹ , n, p, A, Y,
X and m are as defined above. ] A method for producing a heteroarylhydrazone compound represented by the formula: 23. The following general formula (XI): [Wherein, R ¹ is a C ₁ -C ₆ alkyl group (the alkyl group may be substituted with the same or different 1 to 5 halogen atoms), a C ₂ -C ₆ alkenyl group (the The alkenyl group may be the same or different from 1 to 3
May be substituted by halogen atoms. ), C ₂
-C ₆ alkynyl group, phenyl group ｛The phenyl group is
1 to 5 identical or different halogen atoms, C ₁
A C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is the same or different 1 to 5 halogen atoms) May be substituted with 5 halogen atoms) or a cyano group. {Or 5- or 6-membered heterocyclic group} The heterocyclic group contains at least one nitrogen atom, oxygen atom or sulfur atom and is the same or different from 1 to 3
Halogen atoms, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is Same or different 1 to 5
May be substituted by halogen atoms. ) Or a cyano group. And R ² and R ³ are the same or different and represent a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a halogen atom or a cyano group, or R ² and R ³ Is a C ₃ -C ₇ cycloalkyl group together with these bonding carbon atoms. The cycloalkyl group is the same or different 1 to 5 C ₁ -C ₆ alkyl groups (the alkyl group is same or different 1 to may have five substituted by halogen atom.), C ₂ ~C ₆ alkenyl group (said alkenyl group may be substituted by 1 to 3 identical or different halogen atoms ), A C ₁ -C ₆ alkoxy group (where the alkoxy groups are the same or different
And may be substituted with from 5 to 5 halogen atoms. )
Or it may be substituted by a halogen atom. May form}, A represents an oxygen atom, a group {wherein represented by a sulfur atom or the formula N-R ^6, R ⁶ is a hydrogen atom, a halogen atom,
A C ₁ -C ₆ alkyl group (the alkyl group may be substituted by 1 to 5 identical or different halogen atoms), a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, _A C ₁ -C ₆ alkoxy group (the alkoxy group may be substituted by the same or different 1 to 5 halogen atoms), a C ₂ -C ₆ alkenyloxy group,
C ₂ -C ₆ alkynyloxy group, C ₁ -C ₆ alkylthio group (the alkylthio group may be substituted by the same or different 1 to 5 halogen atoms), phenyl group, phenoxy group, phenylthio group shows a formyl group, C ₂ -C ₆ alkylcarbonyl group, a nitro group or a cyano group. Ｐ, p represents 0, 1 or 2, Y
Is halogen atom, C ₁ -C ₆ alkyl group (the alkyl group may be substituted by same or different 1 to 5 halogen atoms.), C ₂ ~C ₆ alkenyl, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ alkoxy group (the alkoxy group may be substituted by the same or different 1 to 5 halogen atoms), C ₂ -C ₆
Alkenyloxy groups, C ₂ -C ₆ alkynyloxy groups, C
₁ -C ₆ alkylthio group (said alkylthio group may be substituted by same or different 1 to 5 halogen atoms.), A phenyl group, a phenoxy group, a phenylthio group, a formyl group, C ₂ -C ₆ alkyl A carbonyl group, a nitro group or a cyano group, and when p is 2,
A plurality of Y may be the same or different, and R ⁴ and R ⁵ are the same or different and are a hydrogen atom, C ₁ -C ₆
An alkyl group (the alkyl group may be the same or different 1 to 5 halogen atoms or 1 C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, C ₂ -C ₇ alkoxycarbonyl group, pyridyloxy A C ₂ -C ₆ alkenyl group (the alkenyl group may be substituted with the same or different 1 to 3 halogen atoms), C
₂ -C ₆ alkynyl group, a formyl group, C ₂ -C ₁₀ alkylcarbonyl group {said alkyl group being the same or different 1 to 5 halogen atoms or one C ₁
-C ₆ alkoxy group, phenoxy group (the phenoxy group may be substituted by the same or different 1 to 5 C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms), C ₁ -C ₆ alkylthio group, phenylthio group (the phenylthio group may be substituted by _{1 to} 5 identical or different C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. ), A carboxyl group, a C ₂ -C ₇ alkoxycarbonyl group or a cyano group. ｝,
C ₃ -C ₇ alkenylcarbonyl group (said alkenyl group is the same or different 1 to 5 halogen atoms or one phenyl group or C ₂ -C ₇ alkoxycarbonyl group may be substituted.), C ₃ ~
C ₇ alkynyl group, a benzoyl group (the benzoyl group is substituted by the same or different 1 to 5 halogen atoms or C ₁ -C ₆ alkyl group or one carboxyl group or C ₂ -C ₇ alkoxycarbonyl group ), A pyridylcarbonyl group (the pyridylcarbonyl group may be substituted by the same or different 1 to 4 halogen atoms or a C ₁ -C ₆ alkyl group), a thienylcarbonyl group (the thienylcarbonyl group may be substituted by 1 to 3 identical or different halogen atoms or C ₁ -C ₆ alkyl group.), C ₂ -C ₇ alkyl (thiocarbonyl)
Group {-C (= S) -} , phenyl (thiocarbonyl) group {-C (= S) -} , C 2 ~C 7 alkoxycarbonyl group (the alkoxy group may be the same or different 1 to 5 May be substituted with one halogen atom or one C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group or cyano group), C ₃ -C ₇ alkenyloxycarbonyl group, phenoxycarbonyl group (the phenoxy carbonyl group) carbonyl group, the same or different 1 to 5 halogen atoms or C ₁ -C ₆ alkyl group may be substituted.), C ₂ ~C ₇ (alkylthio) carbonyl group {-S-C (= O ) -}, (phenylthio) carbonyl group, C ₂ -C ₇ alkyl dithio group, a phenyl dithio group, C ₃ -C ₈ alkylcarbonyl carbonyl , Phenylcarbonyl group, C ₃ -C ₈ alkoxycarbonyl group, a phenoxycarbonyl group, an amino group {said aminocarbonyl group being the same or different one or two C ₁ ~
C ₆ alkyl group, C ₂ -C ₇ alkoxycarbonyl group,
(C ₂ -C ₇ alkoxycarbonyl) substituted by a C ₁ -C ₆ alkyl group or one phenyl group (the phenyl group may be substituted by the same or different 1 to 5 halogen atoms). May be. ｝, An aminothiocarbonyl group (the aminothiocarbonyl group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups), a furanylcarbonyl group (the furanylcarbonyl group is May be substituted by the same or different 1 to 3 halogen atoms.),
Pyrazolyl group (the pyrazolyl group may be substituted by same or different 1 or 2 C ₁ -C ₆ alkyl group or a halogen atom.),
C ₁ -C ₆ alkylsulfonyl group, phenylsulfonyl group (the phenylsulfonyl group is substituted with _{1 to} 5 identical or different C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxy groups or halogen atoms. Or an aminosulfonyl group (the aminosulfonyl group may be substituted by the same or different one or two C ₁ -C ₆ alkyl groups), or R ⁴ and R ⁵ are the same. Together, a methylidene group—the methylidene group may be the same or different and one or two C ₁ -C ₆ alkyl groups, wherein the alkyl group is substituted by the same or different 1 to 5 halogen atoms. which may be.), phenyl group (said phenyl group may be the same young are selected from C ₁ -C ₆ alkyl group, the group consisting of halogen atom and C ₁ -C ₆ alkoxy group Ku may be substituted by 1 to 5 substituents different.), A halogen atom, C ₂ -C ₇ alkoxycarbonyl group, phenoxycarbonyl group or amino group {said amino group may be the same or different 1 or Two C ₁ -C ₆ alkyl groups or (C ₁ -C ₆ alkoxy) C _1-
It may be substituted by a C ₆ alkyl group. ｝ May be substituted. Or R ⁴ and R ⁵ together with the nitrogen atom to which they are attached form succinimide, phthalimide or pyrrole-2,5-dione;
Is a halogen atom, a C ₁ -C ₆ alkyl group (the alkyl group may be substituted by the same or different 1 to 5 halogen atoms), a C ₁ -C ₆ alkoxy group (the alkoxy group is Same or different 1 to 5
May be substituted by halogen atoms. ), C ₂
-C ₇ alkoxycarbonyl group or (C ₁ -C ₆ alkyl) aminocarbonyl group (said alkylaminocarbonyl group, the same or different 1 to 5 halogen atoms may be substituted.) Indicates, m is 1,
2, 3, 4 or 5 is indicated. A heteroarylhydrazone compound represented by the following general formula (I): [Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , p, A, Y, X and m have the same meanings as described above, and n represents 0, 1 or 2]. ] A method for producing a heteroarylhydrazone compound represented by the formula: