JPH10338668A - Oxime-based compound, its use and intermediate for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a new oxime-based compound, having excellent insecticidal and acaricidal activities and useful as an insecticide and acaricide. SOLUTION: This oxime-based compound is represented by formula I R<1> to R<3> are each a halogen, an alkyl or the like; R<4> is a 3,3-dihalogeno-2-propenyl; (a) is 0-2; Y is O, S or NH; Z is O, S; R<6> is H, an alkyl or the like; A is represented by formula II [R<19> to R<21> are each H, an alkyl or the like; R<22> is H, an alkyl or the like; (h) is 0 or 1; (i) is 1-6], etc.}, e.g. 4-[2,6-dichloro-4-(3,3- dichloro-2-propenyloxy)phenoxy]butanal O-isopropyloxime. The compound represented by formula I is obtained by reacting, e.g. a new phenolic compound represented by formula III (R<7> is H, an alkyl or the like; R<31> is R<6> other than H) with an alcohol compound represented by the formula, HO-R in the presence of a suitable dehydrating agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an oxime compound,
It relates to its use and its production intermediate.

2. Description of the Related Art It has been reported that certain oxime compounds can be used as active ingredients in insecticides.
No. 33 is described. However, these compounds are not always sufficient as active ingredients of insecticides and miticides in terms of insecticidal efficacy and the like.

[0002]

Means for Solving the Problems The present inventors have made the above-mentioned conditions.
In view of the situation, we have found compounds with excellent insecticidal and acaricidal efficacy.
As a result of intensive studies to obtain the value, it is expressed by the following equation (1).
Oxime compounds have excellent insecticidal and acaricidal activity
This led to the completion of the present invention. That is,
The present invention relates to formula (1)中 where R¹, R^TwoAnd R^ThreeAre independently halo
Gen atom, alkyl group having 1 to 3 carbon atoms, 1 to 3 carbon atoms
3 haloalkyl groups, alkoxy groups having 1 to 3 carbon atoms,
A haloalkoxy group having 1 to 3 carbon atoms, a nitro group or
Represents an ano group;^FourIs 3,3-dihalogeno-2-prope
A represents an integer of 0 to 2, and Y represents an oxygen atom
Z represents an oxygen atom, a sulfur atom or a sulfur atom
Atom or NR^FiveR represents a group^FiveIs hydrogen atom, acetyl group
Or an alkyl group having 1 to 3 carbon atoms;⁶Is hydrogen
Atom, alkyl group having 1 to 8 carbon atoms, 2 to 6 carbon atoms
Haloalkyl group, alkenyl group having 3 to 6 carbon atoms, carbon
A haloalkenyl group having 3 to 6 carbon atoms,
A quinyl group, a haloalkynyl group having 3 to 6 carbon atoms or
Represents a phenylphenyl group, or has 1 to 4 carbon atoms
3 to 7 carbon atoms which may be substituted with an alkyl group
Represents a cycloalkyl group or has 1 ring carbon
Having 4 carbon atoms, which may be substituted with an alkyl group
Or 10 (cycloalkylalkyl) groups, or
Or may be substituted with an alkyl group having 1 to 4 carbon atoms.
Represents a cycloalkenyl group having 5 to 6 carbon atoms, or
Or the ring is substituted with an alkyl group having 1 to 4 carbon atoms.
Which may have 6 to 8 carbon atoms (cycloalkenylalkyl);
) Group, or cyano group, nitro group, (carbon
An alkoxy) carbonyl group having 1 to 4 carbon atoms and 1 to 4 carbon atoms
4 alkylthio groups or alkoxy having 1 to 4 carbon atoms
Carbon substituted by at least one of the groups
Represents an alkyl group of the formulas 1 to 6, or a compound represented by the formula (2)[Wherein (R⁸)_bRepresents 0 to 5 identical or different
A halogen atom, an alkyl group having 1 to 6 carbon atoms, carbon
Haloalkyl group having 1 to 3 atoms, alk having 2 to 6 carbon atoms
Nyl group, haloalkenyl group having 2 to 6 carbon atoms, 2 carbon atoms
To 6 alkynyl groups, haloalkinis having 2 to 6 carbon atoms
Group, an alkoxy group having 1 to 6 carbon atoms, 1 to 3 carbon atoms
Haloalkoxy group, alkenyloxy having 3 to 6 carbon atoms
Si group, haloalkenyloxy group having 3 to 6 carbon atoms, carbon
An alkynyloxy group having 3 to 6 carbon atoms;
Roalkynyloxy group, (alkoxy having 1 to 5 carbon atoms)
B) carbonyl, cyano or nitro;
⁹, R^Ten, R¹¹, R¹², R¹³And R¹⁴Is German
Stands for a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or
Represents a trifluoromethyl group, wherein D is of the formula -CH = or nitrogen
Represents an atom, J represents an oxygen atom or a sulfur atom, and b represents
Represents an integer of 0 to 5, d represents an integer of 1 to 3, e
Represents an integer of 0 to 3, f represents an integer of 2 to 4,
R^FifteenAnd R¹⁸Is an alkyl group having 1 to 6 carbon atoms,
Haloalkyl group having 1 to 3 atoms, alk having 2 to 6 carbon atoms
Represents a nyl group or a cycloalkyl group having 3 to 6 carbon atoms
Or a halogen atom, alkyl having 1 to 4 carbon atoms
Group, haloalkyl group having 1 to 3 carbon atoms, 1 to 4 carbon atoms
An alkoxy group or haloalkoxy having 1 to 3 carbon atoms
R represents a phenyl group which may be substituted with¹⁶You
And R¹⁷Are each independently an alkyl having 1 to 6 carbons
Kill group, haloalkyl group having 2 to 6 carbon atoms, 3 carbon atoms
6 alkenyl groups, haloalkenyl having 3 to 6 carbon atoms
Group, an alkynyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms
Haloalkynyl group or cycloalkyl having 3 to 6 carbon atoms
Represents a halogen group, or a halogen atom, having 1 to 4 carbon atoms.
Alkyl group, haloalkyl group having 1 to 3 carbon atoms, carbon
An alkoxy group having 1 to 4 carbon atoms or a C 1 to 3 carbon atom;
Phenyl group which may be substituted with
Or the ring is a halogen atom, having 1 to 4 carbon atoms.
Alkyl group, haloalkyl group having 1 to 3 carbon atoms, carbon number
An alkoxy group having 1 to 4 or a halo having 1 to 3 carbon atoms
A benzyl group which may be substituted with an alkoxy group
You. T¹, T^Two, T^Three, T^Four, T^Five, T⁶Or
T⁷And R⁷Is a hydrogen atom, an alkyl having 1 to 6 carbon atoms
Group, haloalkyl group having 1 to 3 carbon atoms, or 3 carbon atoms
Represents 6 to 6 cycloalkyl groups, or halogen
Atom, alkyl group having 1 to 4 carbon atoms, 1 to 3 carbon atoms
Haloalkyl group, alkoxy group having 1 to 3 carbon atoms or
Is substituted with a haloalkoxy group having 1 to 3 carbon atoms,
Represents a phenyl group, or the ring is a halogen atom.
, An alkyl group having 1 to 4 carbon atoms, a halo having 1 to 3 carbon atoms.
A loalkyl group, an alkoxy group having 1 to 3 carbon atoms or
Even when substituted with a haloalkoxy group having 1 to 3 carbon atoms.
Represents a good benzyl group, or a cyano group or
Represents an alkoxy) carbonyl group having a prime number of 1 to 4, or
Or an alkyl group having 1 to 3 carbon atoms substituted with one cyano group.
Represents an alkyl group or one (C 1 -C 4)
1 to 3 carbon atoms substituted with an alkoxy) carbonyl group
A represents an alkyl group of the formula (3)¹:-( CR¹⁹= CR²⁰)_h― (CR^{twenty one}R^{twenty two})_i-A^Two:-( CR¹⁹= CR²⁰)_h― (CR^{twenty one}R^{twenty two})_j―Q¹-G- [wherein, R¹⁹, R²⁰And R^{twenty one}Are each independently water
A hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or
Oromethyl group, R^{twenty two}Is a hydrogen atom and has 1 to 3 carbon atoms
Represents an alkyl group or a trifluoromethyl group,
Or A¹In the above, h is 0 and i is 1.
If R^{twenty two}And R⁷Is bonded at the terminal,
Trimes optionally substituted with alkyl groups of formulas 1 to 3
Forming Tylene, Tetramethylene and Pentamethylene groups
Or A^TwoWhether h is 0
If one j is 1, then R^{twenty two}And R⁷And are bound at the end
And is substituted by an alkyl group having 1 to 3 carbon atoms.
Trimethylene group, tetramethylene group, pentame
A tylene group may be formed. h represents an integer of 0 or 1
And i represents an integer of 1 to 6, and j represents an integer of 1 to 3.
Represents, Q¹Is an oxygen atom, S (O)_yGroup or NR²⁹Represents a group,
R²⁹Represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
And y represents an integer from 0 to 2, and G represents the formula (4) G¹:-( CR^{twenty three}R^{twenty four})_k-G^Two:-( CR^{twenty three}R^{twenty four})_m―CR^{twenty five}= CR²⁶― (CR²⁷R²⁸)_n-G^Three:-( CR^{twenty three}R^{twenty four})_m―C≡C― (CR^{twenty five}R²⁶)_n-G^Four:-( CR^{twenty three}R^{twenty four})_p-E- (CR^{twenty five}R²⁶)_q-G^Five:-( CR^{twenty three}R^{twenty four})_r―Q^Two― (CR^{twenty five}R²⁶)_s-(Where R^{twenty three}, R^{twenty four}, R^{twenty five}, R²⁶, R²⁷And R²⁸Is
Each independently a hydrogen atom, an alkyl having 1 to 3 carbon atoms
Or a trifluoromethyl group, and k is 2 to 8
M represents an integer of 1 to 3, and n represents 1 to
Represents an integer of 3, p represents an integer of 0 or 1, and q represents 0
Or represents an integer of 1; r represents an integer of 2 to 4;
Represents an integer of 2 to 4, and Q^TwoIs an oxygen atom, S (O)_zBase
Is NR³⁰R represents a group³⁰Is from a hydrogen atom or carbon number 1
3 represents an alkyl group; z represents an integer of 0 to 2;
Represents a cycloalkylene group having 5 or 6 carbon atoms. )so
G shown¹, G^Two, G ^Three, G^FourOr G^FiveRepresents ]
A¹Or A^TwoRepresents Oxime conversion represented by｝
Compound (hereinafter, referred to as the compound of the present invention) and
Provided are insecticides and acaricides as active ingredients. Also, the formula
Among the compounds represented by (1), R⁶Is a hydrogen atom
Oxime compounds are useful as insecticides and acaricides
Together with R of the compound represented by the formula (1)⁶Is hydrogen
Useful as an intermediate for the production of non-atom oxime compounds
It is.

The present invention further relates to an intermediate for the production of the compound of the present invention.
Formula (5) useful as a body中 where R³¹Is R other than a hydrogen atom⁶Means R¹,
R^Two, R^Three, R⁶, R⁷, A, A and Z are as defined above
Represents We also provide phenolic compounds represented by｝,
The present invention further provides an intermediate for producing the compound of the present invention.
Useful, Formula (6) R³²ON = CR⁷-CR³³R³⁴-OG⁶-L^Four 中 where R⁷Has the same meaning as in claim 1;³²Is carbon
An alkyl group having 1 to 8 carbon atoms and a haloalkyl having 2 to 6 carbon atoms
Alkenyl group having 3 to 6 carbon atoms, 3 to 6 carbon atoms
A alkynyl group having 3 to 6 carbon atoms,
Haloalkynyl group having 3 to 6 carbon atoms or triphenyl
Represents a methyl group or an alkyl having 1 to 4 carbon atoms
C3-C7 cycloalkyl which may be substituted with a group
Represents a kill group, or a ring moiety having 1 to 4 carbon atoms.
Having 4 to 10 carbon atoms, which may be substituted with a kill group.
Represents a (cycloalkylalkyl) group or carbon
Carbon number which may be substituted by an alkyl group of formulas 1 to 4
Represents 5 to 6 cycloalkenyl groups, or
May be substituted with an alkyl group having 1 to 4 carbon atoms
Represents a (cycloalkenylalkyl) group having 6 to 8 carbon atoms
Or T in equation (2)¹, T^TwoOr T^ThreeTo
Represents, R³³Is a hydrogen atom or an alkyl having 1 to 3 carbon atoms
R represents a group³⁴Is a hydrogen atom or an alkyl having 1 to 3 carbon atoms
Represents a kill group, or R³⁴And R ⁷And bind at the end
Is substituted by an alkyl group having 1 to 3 carbon atoms.
Trimethylene group, tetramethylene group, pen
A Tamethylene group may be formed. L^FourIs hydroxyl group, chlorine source
Atom, bromine atom, iodine atom, methanesulfonyloxy group
Or a p-toluenesulfonyloxy group;⁶Is
Formula (22) G⁷:-( CR⁴¹R⁴²)_k-G⁸:-( CR⁴¹R⁴²)_m―CR⁴³= CR⁴⁴― (CR⁴⁵R⁴⁶)_n-G⁹:-( CR⁴¹R⁴²)_m―C≡C― (CR⁴³R⁴⁴)_n-(Where R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵And R⁴⁶Is
Each independently represents a hydrogen atom or an alkyl having 1 to 3 carbon atoms;
Represents a kill group, k represents an integer of 2 to 8, and m represents 1 to
Represents an integer of 3, and n represents an integer of 1 to 3. )
G⁷, G⁸Or G⁹Represents The compound represented by｝
Also provide.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, R ¹ , R ² , R ³
And the halogen atom represented by R ⁸ is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,
R ¹ , R ² , R ³ , R ⁵ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ ,
R ¹⁴ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , R
^{26, R 27, R 28,} R 29, R 30, R 33, R 34, R 41,
The alkyl group having 1 to 3 carbon atoms represented by R ⁴² , R ⁴³ , R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ is a methyl group, an ethyl group, an n-propyl group or an isopropyl group,
^6, represented by R ³¹ and R ^32, the alkyl group having 1 to 8 carbon atoms, e.g., methyl group, ethyl group, n- propyl group, an isopropyl group, n- butyl group, isobutyl group, sec- butyl group Tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-
Pentyl group, 1-ethylpropyl group, n-hexyl group,
Isohexyl group, 2-ethylbutyl group, 1-methylpentyl group, 1-ethylbutyl group, 3-methylpentyl group,
1,3-dimethylbutyl group, n-heptyl group, 1-ethyl-1-methylbutyl group, n-octyl group, 1-methylheptyl group, and the like, and R ⁷ , R ⁸ , R ¹⁵ , R ¹⁶ , R ¹⁷ And the alkyl group having 1 to 6 carbon atoms represented by R ¹⁸ include, for example, a methyl group, an ethyl group, an n-propyl group,
Isopropyl group, n-butyl group, isobutyl group, sec
-Butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1-ethylpropyl group, n-hexyl group, isohexyl group, 2-ethylbutyl group, 1-methylpentyl group,
1-ethylbutyl group, 3-methylpentyl group, 1,3-
A dimethylbutyl group or the like, and R ¹ , R ² , R ³ , R ⁷ ,
The haloalkyl group having 1 to 3 carbon atoms represented by R ⁸ , R ¹⁵ and R ¹⁸ is, for example, a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group,
1-fluoroethyl group, 1-chloroethyl group, 1-bromoethyl group, perfluoroethyl group, 2-bromo-1,
1,2,2-tetrafluoroethyl group, 1,1,2,2
-Tetrafluoroethyl group, 2-chloro-1,1,2-
Trifluoroethyl group, 2-bromo-1,1,2-trifluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 2,2,2-tribromoethyl Group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group,
2,2-difluoroethyl group, 2,2-dichloroethyl group, 2,2-dibromoethyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, 3
-Iodopropyl group, 3,3,3-trifluoropropyl group, 2,2,2,3,3,3-hexafluoropropyl group, 1,1,1,3,3,3-hexafluoro-2-
Propyl group, 2-fluoropropyl group, a 2-chloropropyl group, 2-bromopropyl group, 2-iodo-propyl group, 2,3-dibromopropyl group and the like, R ^6,
The haloalkyl group having 2 to 6 carbon atoms represented by R ¹⁶ , R ¹⁷ , R ³¹ and R ³² includes, for example, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, , 2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2
-Iodoethyl group, 2,2-difluoroethyl group, 2,
2-dichloroethyl group, 2,2-dibromoethyl group, 3
-Fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, 3-iodopropyl group, 3,3,3-
Trifluoropropyl group, 2,2,2,3,3,3-hexafluoropropyl group, 1,1,1,3,3,3-hexafluoro-2-propyl group, 2-fluoropropyl group, 2- Chloropropyl group, 2-bromopropyl group, 2
-Iodopropyl group, 2,3-dibromopropyl group, 4
-Fluorobutyl group, 4-chlorobutyl group, 4-bromobutyl group, 4-iodobutyl group, 3-chloro-2,2-
Dimethylpropyl group, 3-bromo-2,2-dimethylpropyl group, 2,2,3,3,4,4,5,5-octafluoropentyl group, 6-chlorohexyl group, 6-bromohexyl group, etc. Yes,

The alkoxy group having 1 to 3 carbon atoms represented by R ¹ , R ² and R ³ is a methoxy group, an ethoxy group, an n-propyloxy group or an isopropyloxy group, and is represented by R ⁸ . The alkoxy group having 1 to 6 carbon atoms includes, for example, methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, n- Pentyloxy group, isopentyloxy group, neopentyloxy group, t
ert-pentyloxy group, 1-ethylpropyloxy group, n-hexyloxy group, isohexyloxy group, 2
-Ethylbutyloxy group, 1-methylpentyloxy group, 1-ethylbutyloxy group, 3-methylpentyloxy group, 1,3-dimethylbutyloxy group and the like;
Examples of the haloalkoxy group having 1 to 3 carbon atoms represented by ¹ , R ² , R ³ and R ⁸ include a trifluoromethoxy group, a bromodifluoromethoxy group, a 1-fluoroethoxy group, a 1-chloroethoxy group, 1-bromoethoxy group, perfluoroethoxy group, 2-bromo-1,1,1
2,2-tetrafluoroethoxy group, 1,1,2,2-
Tetrafluoroethoxy group, 2-chloro-1,1,2-
Trifluoroethoxy group, 2-bromo-1,1,2-trifluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, 2,2
2-tribromoethoxy group, 2-fluoroethoxy group,
2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2-difluoroethoxy group, 2,
2-dichloroethoxy group, 2,2-dibromoethoxy group, 3-fluoropropyloxy group, 3-chloropropyloxy group, 3-bromopropyloxy group, 3-iodopropyloxy group, 3,3,3-trifluoro Propyloxy group, 2,2,2,3,3,3-hexafluoropropyloxy group, 1,1,1,3,3,3-hexafluoro-2-propyloxy group, 2-fluoropropyloxy group, 2-chloropropyloxy group, 2-bromopropyloxy group, 2-iodopropyloxy group, 2,3-
A dibromopropyloxy group or the like, and R ⁶ , R ¹⁶ ,
The alkenyl group having 3 to 6 carbon atoms represented by R ¹⁷ , R ³¹ and R ³² includes, for example, allyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group,
2-methyl-2-propenyl group, 2-pentenyl group, 3
-Pentenyl group, 4-pentenyl group, 1-methyl-2-
Butenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-
Methyl-3-butenyl group, 3-methyl-3-butenyl group, 1-ethyl-2-propenyl group, 2-ethyl-2-
A propenyl group, a 2-hexenyl group, a 3-hexenyl group,
4-hexenyl group, 5-hexenyl group, 1-methyl-2
-Pentenyl group, 2-methyl-2-pentenyl group, 3-
Methyl-2-pentenyl group, 4-methyl-2-pentenyl group, 1-methyl-3-pentenyl group, 2-methyl-3
-Pentenyl group, 3-methyl-3-pentenyl group, 4-
Methyl-3-pentenyl group, 1-methyl-4-pentenyl group, 2-methyl-4-pentenyl group, 3-methyl-4
-Pentenyl group, 4-methyl-4-pentenyl group and the like, represented by R ⁶ , R ¹⁶ , R ¹⁷ , R ³¹ and R ³² ;
A haloalkenyl group having 3 to 6 carbon atoms is, for example, 3
-Chloro-2-propenyl group, 3-bromo-2-propenyl group, 2-chloro-2-propenyl group, 2-bromo-
2-propenyl group, 3,3-dichloro-2-propenyl group, 3,3-dibromo-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,3-dichloro-2-
A propenyl group, a 2,3-dibromo-2-propenyl group,
2-chloromethyl-2-propenyl group, 4-chloro-2
-Butenyl group, 3-chloro-4,4,4-trifluoro-2-butenyl group, 3-bromo-4,4,4-trifluoro-2-butenyl group, 3,4-dichloro-4,4- Difluoro-2-butenyl group, 3,4,4,4-tetrafluoro-2-butenyl group, 4,4-dichloro-3-butenyl group, 4,4-dibromo-3-butenyl group, 5,5-
Dichloro-4-pentenyl group, 5,5-dibromo-4-
A pentenyl group, a 6,6-dichloro-5-hexenyl group,
A 6,6-dibromo-5-hexenyl, R ^6,
The alkynyl group having 3 to 6 carbon atoms represented by R ¹⁶ , R ¹⁷ , R ³¹ and R ³² includes, for example, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2
-Propynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group,
1-methyl-3-butynyl group, 2-methyl-3-butynyl group, 1-ethyl-2-propynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, 1-ethyl -2-butynyl group, 1-ethyl-3
-Butynyl group, 2-ethyl-3-butynyl group and the like,
The haloalkynyl group having 3 to 6 carbon atoms represented by R ⁶ , R ¹⁶ , R ¹⁷ and R ³² is, for example, 3-chloro-
2-propynyl group, 3-bromo-2-propynyl group, 4
-Chloro-2-butynyl group, 4-chloro-3-butynyl group, 4-bromo-2-butynyl group, 4-bromo-3-butynyl group, 5-chloro-4-pentynyl group, 4-chloro-1- Methyl-2-butynyl group, 4-chloro-1-methyl-3-butynyl group, 4-chloro-2-methyl-3-butynyl group, 5-bromo-4-pentynyl group, 4-bromo-1-methyl- 2-butynyl, 4-bromo-1-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 6-chloro-5-hexynyl, 6-bromo-5-hexynyl, etc. And the alkenyl group having 2 to 6 carbon atoms represented by R ⁸ , R ¹⁵ and R ¹⁸ is, for example, a vinyl group, a 1-propenyl group, an isopropenyl group,
1-butenyl group, allyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-
2-propenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group,
2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-methyl-3-
Butenyl group, 3-methyl-3-butenyl group, 1-ethyl-2-propenyl group, 2-ethyl-2-propenyl group,
2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-methyl-2-pentenyl group, 2-methyl-2-pentenyl group, 3-methyl-2-
Pentenyl group, 4-methyl-2-pentenyl group, 1-methyl-3-pentenyl group, 2-methyl-3-pentenyl group, 3-methyl-3-pentenyl group, 4-methyl-3-
A pentenyl group, a 1-methyl-4-pentenyl group, a 2-methyl-4-pentenyl group, a 3-methyl-4-pentenyl group, a 4-methyl-4-pentenyl group or the like, and having 2 carbon atoms represented by R ⁸ To 6 are haloalkenyl groups, for example, a 2-chloroethenyl group, a 2-bromoethenyl group,
2,2-dichloroethenyl group, 2,2-dibromoethenyl group, 3-chloro-2-propenyl group, 3-bromo-2
-Propenyl group, 2-chloro-2-propenyl group, 2-
Bromo-2-propenyl group, 3,3-dichloro-2-propenyl group, 3,3-dibromo-2-propenyl group,
3,3-difluoro-2-propenyl group, 2,3-dichloro-2-propenyl group, 2,3-dibromo-2-propenyl group, 2-chloromethyl-2-propenyl group, 4-
Chloro-2-butenyl group, 3-chloro-4,4,4-trifluoro-2-butenyl group, 3-bromo-4,4,4
-Trifluoro-2-butenyl group, 3,4-dichloro-
4,4-difluoro-2-butenyl group, 3,4,4,4
-Tetrafluoro-2-butenyl group, 4,4-dichloro-3-butenyl group, 4,4-dibromo-3-butenyl group, 5,5-dichloro-4-pentenyl group, 5,5-dibromo-4- A pentenyl group, a 6,6-dichloro-5-hexenyl group, a 6,6-dibromo-5-hexenyl group, and the like. The alkynyl group having 2 to 6 carbon atoms represented by R ⁸ includes, for example, ethynyl group, -Propynyl group, 1-
Butynyl group, 2-propynyl group, 2-butynyl group, 3-
Butynyl group, 1-methyl-2-propynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-
Methyl-2-butynyl group, 1-methyl-3-butynyl group, 2-methyl-3-butynyl group, 1-ethyl-2-propynyl group, 2-hexynyl group, 3-hexynyl group, 4
-Hexynyl group, 5-hexynyl group, 1-ethyl-2-
A butynyl group, a 1-ethyl-3-butynyl group, a 2-ethyl-3-butynyl group, etc., having 2 carbon atoms represented by R ^8.
To 6 are haloalkynyl groups such as 2-chloroethynyl group, 2-bromoethynyl group and 3-chloro-2-
Propynyl group, 3-bromo-2-propynyl group, 4-chloro-2-butynyl group, 4-chloro-3-butynyl group,
4-bromo-2-butynyl group, 4-bromo-3-butynyl group, 5-chloro-4-pentynyl group, 4-chloro-1
-Methyl-2-butynyl group, 4-chloro-1-methyl-
3-butynyl group, 4-chloro-2-methyl-3-butynyl group, 5-bromo-4-pentynyl group, 4-bromo-1
-Methyl-2-butynyl group, 4-bromo-1-methyl-
3-butynyl group, 4-bromo-2-methyl-3-butynyl group, 6-chloro-5-hexynyl group, 6-bromo-5
And a cycloalkyl group having 3 to 6 carbon atoms represented by R ⁷ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ is a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group. ,

The alkenyloxy group having 3 to 6 carbon atoms represented by R ⁸ includes, for example, allyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl-2
-Propenyloxy group, 2-methyl-2-propenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1-methyl-2-butenyloxy group, 2-methyl-2-butenyloxy group , 3
-Methyl-2-butenyloxy group, 1-methyl-3-butenyloxy group, 2-methyl-3-butenyloxy group,
3-methyl-3-butenyloxy group, 1-ethyl-2-
Propenyloxy group, 2-ethyl-2-propenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1-methyl-2-pentenyloxy group, 2- Methyl-2-pentenyloxy group, 3-methyl-2-pentenyloxy group, 4-methyl-2-pentenyloxy group, 1
-Methyl-3-pentenyloxy group, 2-methyl-3-
Pentenyloxy group, 3-methyl-3-pentenyloxy group, 4-methyl-3-pentenyloxy group, 1-methyl-4-pentenyloxy group, 2-methyl-4-pentenyloxy group, 3-methyl-4- Pentenyloxy group,
A haloalkenyloxy group having 3 to 6 carbon atoms represented by R ⁸ is, for example, a 3-chloro-2-propenyloxy group,
3-bromo-2-propenyloxy group, 2-chloro-2
-Propenyloxy group, 2-bromo-2-propenyloxy group, 3,3-dichloro-2-propenyloxy group,
3,3-dibromo-2-propenyloxy group, 3,3-
Difluoro-2-propenyloxy group, 2,3-dichloro-2-propenyloxy group, 2,3-dibromo-2-
Propenyloxy group, 2-chloromethyl-2-propenyloxy group, 4-chloro-2-butenyloxy group, 3-
Chloro-4,4,4-trifluoro-2-butenyloxy group, 3-bromo-4,4,4-trifluoro-2-butenyloxy group, 3,4-dichloro-4,4-difluoro-2-butenyloxy group 3,4,4,4-tetrafluoro-2-butenyloxy group, 4,4-dichloro-3
-Butenyloxy group, 4,4-dibromo-3-butenyloxy group, 5,5-dichloro-4-pentenyloxy group, 5,5-dibromo-4-pentenyloxy group, 6,
A 6-dichloro-5-hexenyloxy group, a 6,6-dibromo-5-hexenyloxy group or the like, and the alkynyloxy group having 3 to 6 carbon atoms represented by R ⁸ includes, for example, a 2-propynyloxy group, 2-butynyloxy group,
3-butynyloxy group, 1-methyl-2-propynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1-methyl-2-butynyloxy group, 1-methyl-3 -Butynyloxy group, 2
-Methyl-3-butynyloxy group, 1-ethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group, 1-ethyl-2-butynyloxy group, 1
-Ethyl-3-butynyloxy group, 2-ethyl-3-butynyloxy group and the like, and the haloalkynyloxy group having 3 to 6 carbon atoms represented by R ⁸ is, for example, a 3-chloro-2-propynyloxy group, 3-bromo-2-propynyloxy group, 4-chloro-2-butynyloxy group,
4-chloro-3-butynyloxy group, 4-bromo-2-
Butynyloxy group, 4-bromo-3-butynyloxy group, 5-chloro-4-pentynyloxy group, 4-chloro-1-methyl-2-butynyloxy group, 4-chloro-1
-Methyl-3-butynyloxy group, 4-chloro-2-methyl-3-butynyloxy group, 5-bromo-4-pentynyloxy, 4-bromo-1-methyl-2-butynyloxy group, 4-bromo-1- A methyl-3-butynyloxy group, a 4-bromo-2-methyl-3-butynyloxy group,
6-chloro-5-hexynyloxy group, 6-bromo-5
-Hexynyloxy group and the like, and the (carbonyl having 1 to 5 carbon atoms) carbonyl group represented by R ⁸ includes, for example, a methoxycarbonyl group, an ethoxycarbonyl group,
-Propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyloxycarbonyl group, tert-butyloxycarbonyl group, n-pentyloxycarbonyl group, isopentyloxycarbonyl group, A neopentyloxycarbonyl group, a tert-pentyloxycarbonyl group, a 1-ethylpropyloxycarbonyl group and the like, and the (carbonyl having 1 to 4 carbon atoms) carbonyl group represented by R ⁷ includes a methoxycarbonyl group and an ethoxycarbonyl group. , N-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyloxycarbonyl group, tert-butyloxycarbo A group, 3 represented by R ^4,
The 3-dihalogeno-substituted-2-propenyl group is, for example,
3,3-dichloro-2-propenyl group, 3,3-dibromo-2-propenyl group, 3-bromo-3-chloro-2-
A propenyl group, a 3-chloro-3-fluoro-2-propenyl group, a 3-bromo-3-fluoro-2-propenyl group and the like, having 1 to 4 carbon atoms and represented by R ⁶ , R ³¹ and R ³² . 3 carbon atoms which may be substituted with an alkyl group
And 7 are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylcyclopentyl, 3-methylcyclopentyl, 2-methylcyclohexyl, 3-methylcyclohexyl, Methylcyclohexyl group,
4-ethylcyclohexyl group, 4-n-propylcyclohexyl group, 4-isopropylcyclohexyl group, 4-
a tert- butyl cyclohexyl group, R ^6, R
^The C 4-10 (cycloalkylalkyl) group represented by ³¹ and R ³² , in which the ring portion may be substituted with an alkyl group having 1 to 4 carbon atoms, is, for example, a cyclopropylmethyl group, Butylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, 1-cyclopropylethyl group, (2-methylcyclopropyl) methyl group, 2- (2-methylcyclopropyl) ethyl group, 2-
A cyclopentylethyl group, a 3-cyclopentylpropyl group, a 2-cyclohexylethyl group, a 3-cyclohexylpropyl group, etc., which are substituted by an alkyl group having 1 to 4 carbon atoms represented by R ⁶ , R ³¹ and R ^32. The cycloalkenyl group having 5 to 6 carbon atoms which may be used includes, for example, 2-cyclopentenyl group, 3-cyclopentenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, 3,5,5-trimethyl-2 -Cyclohexenyl group, 3-methyl-2-cyclohexenyl group or the like;
⁶ , a cycloalkyl group having 6 to 8 carbon atoms, the ring portion of which may be substituted with an alkyl group having 1 to 4 carbon atoms represented by R ³¹ and R ³² is, for example,
(1-cyclopentenyl) methyl group, (2-cyclopentenyl) methyl group, (1-cyclohexenyl) methyl group, (2-cyclohexenyl) methyl group, (3-cyclohexenyl) methyl group, 2- (3 -Cyclohexenyl)
An ethyl group,

[0007] R⁷, R^Fifteen, R¹⁶, R¹⁷And R¹⁸Represented by
A halogen atom, an alkyl group having 1 to 4 carbon atoms,
A haloalkyl group having 1 to 3 carbon atoms;
Lucoxy group or haloalkoxy group having 1 to 3 carbon atoms
Halogen in the phenyl group optionally substituted with
A child is a fluorine, chlorine, bromine or iodine atom
An atom, R⁷, R^Fifteen, R¹⁶, R¹⁷And R¹⁸Represented by
A halogen atom, an alkyl group having 1 to 4 carbon atoms,
A haloalkyl group having 1 to 3 carbon atoms;
Lucoxy group or haloalkoxy group having 1 to 3 carbon atoms
Has 1 carbon atom in the phenyl group which may be substituted with
And 4 alkyl groups are a methyl group, an ethyl group, an n-pro
Pill group, isopropyl group, n-butyl group, sec-butyl
A tert-butyl group or an isobutyl group,
R⁷, R^Fifteen, R¹⁶, R¹⁷And R¹⁸Halo represented by
Gen atom, alkyl group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
3 haloalkyl groups and alkoxy groups having 1 to 3 carbon atoms
Or substituted by a haloalkoxy group having 1 to 3 carbon atoms
A halo having 1 to 3 carbon atoms in an optionally substituted phenyl group
Examples of the alkyl group include a trifluoromethyl group,
Fluoromethyl group, bromodifluoromethyl group, 1-fur
Oroethyl group, 1-chloroethyl group, 1-bromoethyl
Group, perfluoroethyl group, 2-bromo-1,1,2,2
2-tetrafluoroethyl group, 1,1,2,2-tetra
Fluoroethyl group, 2-chloro-1,1,2-trifur
Oroethyl group, 2-bromo-1,1,2-trifluoro
Ethyl group, 2,2,2-trifluoroethyl group, 2,
2,2-trichloroethyl group, 2,2,2-tribromo
Ethyl group, 2-fluoroethyl group, 2-chloroethyl
Group, 2-bromoethyl group, 2-iodoethyl group, 2,2
-Difluoroethyl group, 2,2-dichloroethyl group,
2,2-dibromoethyl group, 3-fluoropropyl group,
3-chloropropyl group, 3-bromopropyl group, 3-yo
Propyl group, 3,3,3-trifluoropropyl
Group, 2,2,2,3,3,3-hexafluoropropyl
Group, 1,1,1,3,3,3-hexafluoro-2-propyl
Propyl group, 2-fluoropropyl group, 2-chloropropyl
A 2-bromopropyl group, a 2-iodopropyl group,
2,3-dibromopropyl and the like;⁷, R^Fifteen, R
¹⁶, R¹⁷And R¹⁸Represented by a halogen atom or carbon
An alkyl group having 1 to 4 carbon atoms, a haloalkyl having 1 to 3 carbon atoms
Group, an alkoxy group having 1 to 3 carbon atoms or 1 carbon atom
From 3 to 3 haloalkoxy groups
The alkoxy group having 1 to 3 carbon atoms in the phenyl group is
Ethoxy, ethoxy, n-propyloxy or i
A propyloxy group;⁷, R^Fifteen, R¹⁶, R¹⁷You
And R¹⁸Represented by a halogen atom having 1 to 4 carbon atoms
Alkyl group, haloalkyl group having 1 to 3 carbon atoms, carbon
An alkoxy group having 1 to 3 carbon atoms or a C 1 to 3 carbon atom;
Phenyl group which may be substituted with
Haloalkoxy group having 1 to 3 carbon atoms
For example, trifluoromethoxy group, bromodifluoromethoxy
Si group, 1-fluoroethoxy group, 1-chloroethoxy
Group, 1-bromoethoxy group, perfluoroethoxy group,
2-bromo-1,1,2,2-tetrafluoroethoxy
Group, 1,1,2,2-tetrafluoroethoxy group, 2-
Chloro-1,1,2-trifluoroethoxy group, 2-butane
Lomo-1,1,2-trifluoroethoxy group, 2,2,
2-trifluoroethoxy group, 2,2,2-trichloro
Ethoxy group, 2,2,2-tribromoethoxy group, 2-
Fluoroethoxy group, 2-chloroethoxy group, 2-bromo
Moethoxy group, 2-iodoethoxy group, 2,2-difur
Oloethoxy group, 2,2-dichloroethoxy group, 2,2
-Dibromoethoxy group, 3-fluoropropyloxy
Group, 3-chloropropyloxy group, 3-bromopropyl
Oxy group, 3-iodopropyloxy group, 3,3,3-
Trifluoropropyloxy group, 2,2,2,3,3
3-hexafluoropropyloxy group, 1,1,1,
3,3,3-hexafluoro-2-propyloxy group,
2-fluoropropyloxy group, 2-chloropropyl
Xy group, 2-bromopropyloxy group, 2-iodopro
Pyroxy group, 2,3-dibromopropyloxy group, etc.
Yes, R⁷, R¹⁶And R¹⁷The ring is represented by halo
Gen atom, alkyl group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
3 haloalkyl groups and alkoxy groups having 1 to 3 carbon atoms
Or substituted by a haloalkoxy group having 1 to 3 carbon atoms
A halogen atom in a benzyl group which may be
A hydrogen atom, a chlorine atom, a bromine atom or an iodine atom,
R⁷, R¹⁶And R¹⁷The ring is represented by a halogen atom
, An alkyl group having 1 to 4 carbon atoms, a halo having 1 to 3 carbon atoms.
A loalkyl group, an alkoxy group having 1 to 3 carbon atoms or
Even when substituted with a haloalkoxy group having 1 to 3 carbon atoms.
A C1-4 alkyl group in a good benzyl group;
Are methyl, ethyl, n-propyl, isopropyl
Group, n-butyl group, sec-butyl group, tert-butyl group
A tyl or isobutyl group,⁷, R¹⁶And R
¹⁷Wherein the ring is a halogen atom and has 1 to 4 carbon atoms
Alkyl group, haloalkyl group having 1 to 3 carbon atoms, carbon
An alkoxy group having 1 to 3 carbon atoms or a C 1 to 3 carbon atom;
Benzyl group which may be substituted with
The haloalkyl group having 1 to 3 carbon atoms is, for example,
Trifluoromethyl group, difluoromethyl group, bromodi
Fluoromethyl group, 1-fluoroethyl group, 1-chloro
Ethyl group, 1-bromoethyl group, perfluoroethyl
Group, 2-bromo-1,1,2,2-tetrafluoroethyl
Group, 1,1,2,2-tetrafluoroethyl group, 2-
Chloro-1,1,2-trifluoroethyl group, 2-bromo
Mo-1,1,2-trifluoroethyl group, 2,2,2-
Trifluoroethyl group, 2,2,2-trichloroethyl
Group, 2,2,2-tribromoethyl group, 2-fluoro
Butyl, 2-chloroethyl, 2-bromoethyl, 2
-Iodoethyl group, 2,2-difluoroethyl group, 2,
2-dichloroethyl group, 2,2-dibromoethyl group, 3
-Fluoropropyl group, 3-chloropropyl group, 3-bu
Lomopropyl group, 3-iodopropyl group, 3,3,3-
Trifluoropropyl group, 2,2,2,3,3,3-he
Xafluoropropyl group, 1,1,1,3,3,3-he
Xafluoro-2-propyl group, 2-fluoropropyl
Group, 2-chloropropyl group, 2-bromopropyl group, 2
An iodopropyl group, a 2,3-dibromopropyl group or the like;
Yes, R⁷, R¹⁶And R¹⁷The ring is represented by halo
Gen atom, alkyl group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
3 haloalkyl groups and alkoxy groups having 1 to 3 carbon atoms
Or substituted by a haloalkoxy group having 1 to 3 carbon atoms
Alcohol having 1 to 3 carbon atoms in benzyl group which may be present
An xy group means a methoxy group, an ethoxy group, an n-propyl
A xy or isopropyloxy group,⁷, R¹⁶
And R¹⁷Where the ring is a halogen atom and carbon number
Alkyl group of 1 to 4, haloalkyl of 1 to 3 carbon atoms
Group, alkoxy group having 1 to 3 carbon atoms or 1 carbon atom
3 which may be substituted with a haloalkoxy group
A haloalkoxy group having 1 to 3 carbon atoms in the
For example, a trifluoromethoxy group, bromodifluoro
Methoxy group, 1-fluoroethoxy group, 1-chloroethoxy
Xy group, 1-bromoethoxy group, perfluoroethoxy
Group, 2-bromo-1,1,2,2-tetrafluoroeth
A xy group, a 1,1,2,2-tetrafluoroethoxy group,
2-chloro-1,1,2-trifluoroethoxy group, 2
-Bromo-1,1,2-trifluoroethoxy group, 2,
2,2-trifluoroethoxy group, 2,2,2-tric
Loroethoxy group, 2,2,2-tribromoethoxy group,
2-fluoroethoxy group, 2-chloroethoxy group, 2-
Bromoethoxy group, 2-iodoethoxy group, 2,2-di
Fluoroethoxy group, 2,2-dichloroethoxy group,
2,2-dibromoethoxy group, 3-fluoropropyl
Xy group, 3-chloropropyloxy group, 3-bromopro
Pyroxy group, 3-iodopropyloxy group, 3,3
3-trifluoropropyloxy group, 2,2,2,3
3,3-hexafluoropropyloxy group, 1,1,
1,3,3,3-hexafluoro-2-propyloxy
Group, 2-fluoropropyloxy group, 2-chloropropyl
Ruoxy group, 2-bromopropyloxy group, 2-iodo
Propyloxy group, 2,3-dibromopropyloxy group
And a cycloalkyl having 5 or 6 carbon atoms represented by E
The alkylene group is, for example, 1,2-cyclohexylene
Group, 1,3-cyclohexylene group, 1,4-cyclohexene
Silene, 1,2-cyclopentylene or 1,3-
A cyclopentylene group,⁶Or R³¹Represented by
Cyano group, nitro group, (alkoxy having 1 to 4 carbon atoms)
B) carbonyl groups and alkylthio groups having 1 to 4 carbon atoms
Or at least one of the alkoxy groups having 1 to 4 carbon atoms
Also has 1 to 6 carbon atoms substituted with one or more groups
The group is, for example, a cyanomethyl group, 1-cyanoethyl
Group, 2-cyanoethyl group, 3-cyanopropyl group, nitro
L-methyl group, 1-nitroethyl group, 1-methyl-1-ni
Troethyl group, methoxycarbonylmethyl group, ethoxy
Carbonylmethyl group, isopropoxycarbonylmethyl
Group, 1- (methoxycarbonyl) ethyl group, 2- (meth
Xoxycarbonyl) ethyl group, methoxymethyl group, ethoxy
Cimethyl group, 1-methoxyethyl group, 2-methoxyethyl
Group, 2-ethoxyethyl group, 2,2-dimethoxyethyl
Group, 2,2-diethoxyethyl group, 2,2-dimethoxy
Cypropyl group, 2,2-diethoxypropyl group, 3,3
-Dimethoxypropyl group, 3,3-diethoxypropyl
Group, 2,3-dimethoxypropyl group, methylthiomethyl
Group, 2-methylthioethyl group, 2,2-di (methylthio
E) an ethyl group or the like;⁷One cyano represented by
An alkyl group having 1 to 3 carbon atoms substituted with a group
For example, a cyanomethyl group, a 1-cyanoethyl group, a 2-cya
A nonethyl group or a 3-cyanopropyl group;⁷In table
One (C1-C4 alkoxy) carbo
The alkyl group having 1 to 3 carbon atoms substituted with a nyl group is
For example, methoxycarbonylmethyl group, ethoxy
Bonylmethyl group, isopropoxycarbonylmethyl group,
1- (methoxycarbonyl) ethyl group, 2- (methoxy
Carbonyl) ethyl group and the like;¹At h is 0
And if i is 1, then R^{twenty two}And R⁷And at the end
By bonding, it is substituted with an alkyl group having 1 to 3 carbon atoms.
Optionally substituted trimethylene group, tetramethylene
R, when forming a pentamethylene group^{twenty two}And R
⁷Is, for example, a trimethylene group, 1-methyltrimethyl
Tylene group, 2-methyltrimethylene group, tetramethylene
Group, 1-methyltetramethylene group, 2-methyltetrame
A Tylene group, a pentamethylene group or the like;^TwoAt h
Is 0 and j is 1, then R^{twenty two}And R⁷And end
To form an alkyl group having 1 to 3 carbon atoms.
Optionally substituted trimethylene group, tetramethylene
R, when forming a pentamethylene group^{twenty two}And R
⁷Is, for example, a trimethylene group, 1-methyltrimethyl
Tylene group, 2-methyltrimethylene group, tetramethylene
Group, 1-methyltetramethylene group, 2-methyltetrame
Such as a tylene group and a pentamethylene group;³⁴And R⁷And
By bonding at the terminal, an alkyl having 1 to 3 carbon atoms
A trimethylene group which may be substituted with a
R when forming a len group or a pentamethylene group³⁴
And R⁷Is, for example, a trimethylene group, 1-methyl
Limethylene group, 2-methyltrimethylene group, tetramethyl
Len group, 1-methyltetramethylene group, 2-methyltet
A ramethylene group and a pentamethylene group.

In a preferred embodiment of the compound of the present invention, oxime compounds wherein Y and Z are both oxygen atoms; oxime compounds wherein a is 0; R ¹ , R ² and R
³ is a halogen atom or an oxime-based compound is an alkyl group having 1 to 3 carbon atoms each independently; A is an oxime compound is A ^1; A is an oxime compound is A ^2; A is a A ² An oxime compound wherein Q ¹ is an oxygen atom; R ⁶ is an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms, and 3 to 6 carbon atoms.
An alkenyl group, a haloalkenyl group having 3 to 6 carbon atoms,
An alkynyl group having 3 to 6 carbon atoms or a haloalkynyl group having 3 to 6 carbon atoms, or 1 to 4 carbon atoms
Is a cycloalkyl group having 3 to 7 carbon atoms which may be substituted with an alkyl group of
A (cycloalkylalkyl) group having 4 to 10 carbon atoms which may be substituted with an alkyl group having 4 to 4 carbon atoms, or a 5 to 6 carbon atom which may be substituted with an alkyl group having 1 to 4 carbon atoms. Or a cycloalkyl group having 6 to 8 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a cyano group or a nitro group. Group,
(Alkoxy having 1 to 4 carbon atoms) A carbonyl group, an alkylthio group having 1 to 4 carbon atoms, or an alkyl group having 1 to 6 carbon atoms substituted with at least one of alkoxy groups having 1 to 4 carbon atoms An oxime compound wherein R ⁶ is a hydrogen atom. An oxime compound wherein R ⁶ is a triphenylmethyl group or T ¹ , T ² or T ³ ; R ⁶ is T ⁴ , T ⁵ , T ⁶ or T ⁷
An oxime compound wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms,
An oxime compound which is a cycloalkyl group having 3 to 6 carbon atoms; R ⁷ is a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, and 1 to 3 carbon atoms.
A phenyl group which may be substituted with an alkoxy group or a haloalkoxy group having 1 to 3 carbon atoms, or a ring portion having a halogen atom, an alkyl group having 1 to 4 carbon atoms, or a haloalkyl having 1 to 3 carbon atoms. Group, 1 to 3 carbon atoms
An oxime compound which is a benzyl group which may be substituted with an alkoxy group or a haloalkoxy group having 1 to 3 carbon atoms; wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl having 1 to 3 carbon atoms A group wherein A is A ¹ , and R ⁶ is an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms,
Or an alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, or a haloalkynyl group having 3 to 6 carbon atoms;
A cycloalkyl group having 3 to 7 carbon atoms which may be substituted with an alkyl group having 4 to 4 carbon atoms, or a ring portion having 4 to 4 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. A (cycloalkylalkyl) group having 10 carbon atoms, a cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring portion having 1 carbon atom. An oxime compound which is a (cycloalkenylalkyl) group having 6 to 8 carbon atoms, which may be substituted with an alkyl group having 4 to 4 carbon atoms; wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or 3 is haloalkyl group, and A is A ¹ ,
And an oxime compound wherein R ⁶ is T ¹ or T ² ;
R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms, and A is A ²
And G is G ¹ (where k is an integer of 2 to 6) or G ² , and R ⁶ is an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms. An alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms or 3 carbon atoms.
Or a haloalkynyl group having 1 to 6 carbon atoms, or 3 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.
Or a cycloalkyl group having 4 to 10 carbon atoms, or a (cycloalkylalkyl) group having 4 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or A cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 6 to 6 carbon atoms which may be substituted in the ring portion with an alkyl group having 1 to 4 carbon atoms. An oxime compound which is a (cycloalkenylalkyl) group of from 8 to 8; R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms, and A is A ² ;
And G is G ¹ (where k is an integer of 2 to 6) or G ²
An oxime compound wherein R ⁶ is T ¹ or T ² ; R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms, and
A is A ² , G is G ¹ (where k is an integer of 2 to 6) or G ² , and R ⁶ is an alkyl group having 1 to 8 carbon atoms, and an alkyl group having 2 to 6 carbon atoms. Haloalkyl group, alkenyl group having 3 to 6 carbon atoms, haloalkenyl group having 3 to 6 carbon atoms, alkynyl group having 3 to 6 carbon atoms or 3 carbon atoms
Or a haloalkynyl group having 1 to 6 carbon atoms, or 3 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.
Or a cycloalkyl group having from 7 to 7 or a ring portion which may be substituted with an alkyl group having 1 to 4 carbon atoms;
A (cycloalkylalkyl) group having 4 to 10 carbon atoms, a cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring moiety There may be substituted with an alkyl group having 1 to 4 carbon atoms, having a carbon number of 6 8 in the compound is (cycloalkenylalkyl) group, an oxime-based compound Q ¹ is an oxygen atom; R ⁷ is a hydrogen atom Is an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms, A is A ² , and G is G ¹
(Where k is an integer from 2 to 6) or G ² and R ⁶ is T ¹ or T ² , an oxime compound in which Q ¹ is an oxygen atom; R ² and R ³ are each Is independently a chlorine atom or an alkyl group having 1 to 3 carbon atoms, a is 0, and R ⁴ is 3,3-dichloro-2-propenyl group or 3,3-dibromo-2
A propenyl group, wherein Y and Z are both oxygen atoms, and R ⁶ is an alkyl group having 1 to 5 carbon atoms,
A haloalkyl group having 2 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, and R ⁷ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or trifluoromethyl And A is A ¹
And R ²¹ and R ²² are both hydrogen atoms;
an oxime-based compound in which h is 0 and i is an integer of 3 to 5; R ² and R ³ are each independently a chlorine atom or an alkyl group having 1 to 3 carbon atoms;
Is 0, and R ⁴ is a 3,3-dichloro-2-propenyl group or a 3,3-dibromo-2-propenyl group, and both Y and Z are oxygen atoms, and
R ⁶ is an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 2 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, and R ⁷ is a hydrogen atom, An alkyl group or a trifluoromethyl group having 1 to 4 carbon atoms, A is A ² , G is G ¹ , and R ²¹ , R ²² , R ²³ and R ²⁴ are all hydrogen; An oxime compound in which h is 0, Q ¹ is an oxygen atom, j is 1 and k is an integer of 3 to 6; A is A ¹ , And R
²¹ and R ²² are both hydrogen atoms, h is 0, i is an integer from 3 to 5, Y and Z are both oxygen atoms, and R ² and R ³ are both A is a chlorine atom, a is 0, R ⁴ is a 3,3-dichloro-2-propenyl group, and R ⁶ is an isopropyl group, an isobutyl group, a sec-butyl group, tert.
-Butyl group, 2,2,2-trifluoroethyl group, 2,
2,2-trichloroethyl group, 2,2,2-tribromoethyl group, 1,1,1,3,3,3-hexafluoro-
An oxime compound which is a 2-propyl group or a 3,3-dichloro-2-propenyl group and R ⁷ is a hydrogen atom; A is A ² , G is G ¹ , and R
²¹ , R ²² , R ²³ and R ²⁴ are all hydrogen atoms, h is 0, Q ¹ is an oxygen atom, and j is 1
And k is an integer from 3 to 6, Y and Z
Are both oxygen atoms, R ² and R ³ are both chlorine atoms, a is 0, and R ⁴ is 3,3
-Dichloro-2-propenyl group, and R ⁶ is isopropyl, isobutyl, sec-butyl, te
rt-butyl group, 2,2,2-trifluoroethyl group,
2,2,2-trichloroethyl group, 2,2,2-tribromoethyl group, 1,1,1,3,3,3-hexafluoro-2-propyl group or 3,3-dichloro-2-propenyl And an oxime compound wherein R ⁷ is a hydrogen atom or a methyl group.

Among the compounds of the present invention, a particularly preferred compound is (187) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal.O-isopropyloxime (169) ) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal-O-isopropyloxime (188) 6- (2,6-dichloro-4- (3,3 -Dichloro-2-propenyloxy) phenoxy) hexanal-O-isopropyloxime (26) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal-O-tert- Butyl oxime (16) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy ) Pentanal O-tert-butyl oxime (134) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal O-tert-butyl oxime (189) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal.O- (2,2,2-trichloroethyl) oxime (170) 5- (2,6-dichloro- 4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (2,2,2-trichloroethyl) oxime (190) 6- (2,6-dichloro-4- (3,3- Dichloro-2-propenyloxy) phenoxy) hexanal.O- (2,2,2-trichloroethyl) oxime (24) 4- (2,6-dichloro-4-) 3,3-dichloro-2-propenyloxy) phenoxy) butanal.O- (3,3-dichloro-2-propenyl) oxime (17) 5- (2,6-dichloro-4- (3,3-dichloro- 2-propenyloxy) phenoxy) pentanal O- (3,3-dichloro-2-propenyl) oxime (76) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy ) Hexanal O- (3,3-dichloro-2-propenyl) oxime (165) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde.O -Isopropyl oxime (152) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyl Xyacetaldehyde / O-isopropyl oxime (191) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone / O-isopropyl oxime (172) 5- (2 , 6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-isopropyloxime (6) 4- (2,6-dichloro-4- (3,3-dichloro-) 2-propenyloxy) phenoxy) butyloxyacetaldehyde / O-tert-butyloxime (14) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde / O -Tert-butyloxime (103) 4- (2,6-dichloro-4- (3 , 3-Dichloro-2-propenyloxy) phenoxy) butyloxyacetone / O-tert-butyloxime (104) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) Pentyloxyacetone / O-tert-butyloxime (167) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde / O- (2,2,2 -Trichloroethyl) oxime (160) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde O- (2,2,2-trichloroethyl) oxime (192) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy B) Butyloxyacetone / O- (2,2,2-trichloroethyl)
Oxime (173) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O- (2,2,2-trichloroethyl) oxime (2) 4 -(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime (15) 5- (2 6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde O- (3,3-dichloro-2-
Propenyl) oxime (46) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime ( 47) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxyphenoxy) pentyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime. Represents the compound number of the present invention described below.)

The compound of the present invention can be produced, for example, by the following (Production method A) to (Production method M). (Production Method A) (Method for producing compound in which R ⁶ is other than a hydrogen atom) Formula (7) [Wherein, R ¹ , R ² , R ³ , R ⁶ , R ⁷ , a, A, Y and Z represent the same meaning as described above. Among the compounds represented by], R ⁶ is not hydrogen atom compound (Formula (4) a compound represented by) the formula (8) in L-R ⁴ [wherein, R ⁴ is as defined above L represents a halogen atom (for example, a chlorine atom, a bromine atom, an iodine atom, etc.), a mesyloxy group or a tosyloxy group. A method of reacting with the compound represented by the formula The reaction is preferably performed in an inert solvent in the presence of a suitable base. Examples of the solvent include ketones such as acetone, methyl ethyl ketone and cyclohexanone, 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (for example, C ₁ -C ₄ ).
Ethers such as ethers (eg, diethyl ether, diisopropyl ether, etc.), polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile, nitromethane, dichloromethane, chloroform, 1,2
-Halogenated hydrocarbons such as dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; water; and mixed solvents thereof can also be used. Examples of the base include alkali metal or alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, and alkali metals and alkalis such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate. Earth metal carbonates,
Lithium hydride, sodium hydride, potassium hydride,
Alkali metal or alkaline earth metal hydrides such as calcium hydride, alkali metal alkoxides (eg, C ₁ -C ₄ ) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine; Is raised. If necessary, a catalyst such as an ammonium salt (eg, triethylbenzylammonium chloride) may be added to the reaction system according to the formula (7).
May be added in an amount of 0.01 to 1 mol per 1 mol of the compound represented by the formula (1). The reaction temperature can usually range from -20 ° C to the boiling point of the solvent used in the reaction or 150 ° C, but more preferably from -5 ° C to the boiling point of the solvent used in the reaction or 100 ° C. The molar ratio of the starting material and the base to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio. After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent, concentration, etc., to isolate the target compound of the present invention. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production method B) (In the compound of the present invention, Y
There is an oxygen atom, among the compounds represented by the manufacturing process) the formula of compounds other than R ⁶ is a hydrogen atom (7), Y is an oxygen atom, a compound of formula R ⁶ is not hydrogen atom (9) HO-R ⁴ wherein, R ⁴ are as defined above. A method of reacting with an alcohol compound represented by the formula: The reaction is preferably carried out in the presence of a suitable dehydrating agent, if necessary, in an inert solvent. Examples of the dehydrating agent include dicyclohexylcarbodiimide, dialkyl (eg, C ₁ -C ₄ ) azodicarboxylate (diethyl azozocarboxylate, diisopropyl azodicarboxylate, etc.)-Trialkyl (ex. C ₁ -C ₂₀ ). Examples include phosphine or triarylphosphine (triphenylphosphine, trioctylphosphine, tributylphosphine, etc.). Examples of the solvent include hydrocarbons such as benzene, xylene, and toluene, diethyl ether,
Examples thereof include ethers such as diisopropyl ether, tetrahydrofuran, and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene. The reaction temperature is -2
It can range from 0 ° C. to 200 ° C. or the boiling point of the solvent used in the reaction. The molar ratio of the raw material and the dehydrating agent to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio. After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production method C) (In the compound of the present invention, Y
And Z are both oxygen atoms, and R ⁶ is a compound other than a hydrogen atom. Wherein R ¹ , R ² , R ³ , R ⁴ and a have the same meaning as described above. And a compound represented by the formula (11): R ⁶ O—N ＝ CR ⁷ -AL wherein R ⁶ , R ⁷ , A and L represent the same meaning as described above. Wherein R ⁶ is not a hydrogen atom (of the compounds represented by the formula (6),
⁴ is a chlorine, bromine, iodine, methanesulfonyloxy or p-toluenesulfonyloxy group). The reaction is preferably performed in an inert solvent in the presence of a suitable base.
As the solvent, acetone, methyl ethyl ketone, ketones such as cyclohexanone, 1,2-dimethoxyethane,
Ethers such as tetrahydrofuran, dioxane, dialkyl (for example, C ₁ -C ₄ ) ether (for example, diethyl ether, diisopropyl ether, etc.), N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile, nitromethane Polar solvents, such as dichloromethane, chloroform, 1,2-dichloroethane, chlorobenzene, and the like; halogenated hydrocarbons such as toluene, benzene, xylene, and the like; water; and the like, and a mixed solvent thereof may also be used. it can. As the base, lithium hydroxide, sodium hydroxide, potassium hydroxide, hydroxides of alkali metals or alkaline earth metals such as calcium hydroxide, lithium carbonate, potassium carbonate, sodium carbonate,
Alkali metal or alkaline earth metal carbonates such as calcium carbonate, lithium hydride, sodium hydride, potassium hydride, alkali metal or alkaline earth metal hydrides such as calcium hydride, sodium methoxide,
Alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide (for example, C ₁ -C ₄ );
Organic bases such as triethylamine and pyridine are exemplified. If necessary, a catalyst such as an ammonium salt (eg, triethylbenzylammonium chloride) may be added to the reaction system based on 1 mol of the compound represented by the formula (10).
You may add in the ratio of 0.01 to 1 mol. The reaction temperature can usually range from -20 ° C to the boiling point of the solvent used in the reaction or 150 ° C, but more preferably from -5 ° C to the boiling point of the solvent used in the reaction or 100 ° C. The molar ratio of the starting material and the base to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio. After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production method D) (In the compound of the present invention, Y
And Z are both oxygen atoms, R ⁶ is the preparation of compounds other than hydrogen atoms) Formula (compound represented by 10) and the formula ^{(12) R 6 O-N} = CR 7 -A-OH wherein , R ⁶ , R ⁷ and A represent the same meaning as described above. ]
Wherein R ⁶ is not a hydrogen atom among the compounds represented by the formula (6) (including compounds in which L ⁴ is a hydroxyl group among the compounds represented by the formula (6)). The reaction is
It is preferable to carry out the reaction in the presence of a suitable dehydrating agent, if necessary, in an inert solvent. Examples of the dehydrating agent include dicyclohexylcarbodiimide, dialkyl (for example, C _1-
C ₄ ) azodicarboxylate (diethyl azodicarboxylate, diisopropyl azodicarboxylate, etc.)-Trialkyl (ex. C ₁ -C ₂₀ ) phosphine or triaryl phosphine (triphenyl phosphine, trioctyl phosphine, tributyl phosphine, etc.) ) Systems and the like. Examples of the solvent include hydrocarbons such as benzene, xylene and toluene, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane, or carbon tetrachloride,
Halogenated hydrocarbons such as dichloromethane, chlorobenzene, dichlorobenzene and the like can be mentioned. The reaction temperature can range from -20 ° C to 200 ° C or the boiling point of the solvent used in the reaction. The molar ratio of the raw material and the dehydrating agent to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio. After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production Method E) A hydroxylamine compound represented by the formula (13) R ⁶ O—NH ₂ (where R ⁶ has the same meaning as described above) or a salt thereof, and a compound represented by the formula (14) (Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁷ , A, Y, Z and a have the same meanings as described above). The reaction is carried out in an inert solvent,
The reaction is performed in the presence of a base or an acid as necessary. Examples of the solvent include alcohols such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran and dioxane, acetic acid, water, and the like.
A mixed solvent of these solvents can also be used. Examples of the base include alkali metal or alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, and alkali metals and alkalis such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate. Alkaline metals such as earth metal carbonates, lithium hydride, sodium hydride, potassium hydride and calcium hydride or alkaline earth metal hydrides, sodium methoxide, sodium ethoxide, alkali metal such as potassium tert-butoxide Organic bases such as alkoxides (for example, C ₁ -C ₄ ), triethylamine, pyridine and the like can be mentioned. It is preferable that the reaction is carried out using at least one mole of a base used as necessary with respect to 1 mole of the hydroxylamine-based compound represented by the formula (13). The reaction may be performed in a large excess with respect to the hydroxylamine-based compound represented by the formula (2), so that the role of the base and the solvent can be combined. Examples of the acid include hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, and the like, and the acid is reacted using 0.01 to 1 equivalent with respect to the carbonyl compound represented by the formula (14). be able to. The hydroxylamine-based compound represented by the formula (13) can be used for the reaction as it is, but is usually used in the form of an inorganic acid salt such as a hydrochloride or a sulfate. The reaction temperature can range from −20 ° C. to the boiling point of the solvent used in the reaction or 150 ° C., but is usually preferably from 0 ° C. to the boiling point of the solvent used in the reaction or 60 ° C. The molar ratio of the raw materials and the reagents to be subjected to the reaction can be set arbitrarily. It is preferred to carry out the reaction. After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production method F) (In the compound of the present invention, R
⁶Is a hydrogen atom, T^Four, T^Five, T⁶And T ⁷Other than compound
Manufacturing method) Formula (15) R⁶−L (where R⁶And L represent the same meaning as described above)
Of the compounds⁶Is a hydrogen atom, T^Four, T^Five, T⁶And
And T⁷And a compound of formula (16)(Where R¹, R^Two, R^Three, R^Four, R⁷, A, Y, Z and
a has the same meaning as described above. )
That is, among the compounds of the present invention, R⁶Is a hydrogen atom
To react with The reaction is carried out in the presence of a suitable base
Preferably, the reaction is performed in an inert solvent. As the solvent,
Acetone, methyl ethyl ketone, cyclohexanone, etc.
Ketones, 1,2-dimethoxyethane, tetrahydrof
Orchids, dioxane, dialkyl (eg, C₁-C_FourA)
Ter (eg, diethyl ether, diisopropyl ether
Ethers), N, N-dimethylformami
, Dimethyl sulfoxide, trimethyl hexamethyl phosphate
Amide, sulfolane, acetonitrile, nitromethane, etc.
Polar solvent, dichloromethane, chloroform, 1,2-di
Halogenated hydrocarbons such as chloroethane and chlorobenzene
, Toluene, benzene, xylene and other hydrocarbons
Can include water and the like, and a mixed solvent of these solvents can also be used.
Can be used. As the base, lithium hydroxide
, Sodium hydroxide, potassium hydroxide, calcium hydroxide
Of alkali metal or alkaline earth metal such as
Chloride, lithium carbonate, potassium carbonate, sodium carbonate,
Alkali metal or alkaline earth gold such as calcium carbonate
Genus carbonate, lithium hydride, sodium hydride, water
Alkali metals such as potassium iodide and calcium hydride
Is alkaline earth metal hydride, sodium methoxide,
Sodium ethoxide, potassium tert-butoxide
Alkali metal alkoxides (eg, C₁-C_Four),
Organic bases such as triethylamine and pyridine;
You. If necessary, add ammonium salt (for example,
For example, triethylbenzylammonium chloride)
With respect to 1 mol of the compound represented by the formula (16)
You may add 0.01 to 1 mol ratio. The reaction temperature is
Usually, from -20 ° C to the boiling point of the solvent used for the reaction or 1
The temperature can be in the range of 50 ° C.
More desirable is the boiling point of the solvent used or a temperature up to 100 ° C.
Good. The molar ratio of the raw materials and the base to be used for the reaction is arbitrary.
The reaction can be set at equimolar or near
This is advantageous. After completion of the reaction, the reaction solution is extracted with an organic solvent.
Perform the usual post-treatment operations such as extraction and concentration to achieve the objective of the present invention.
The compound can be isolated. The compound is a chromatographic compound.
Further purification by operations such as laffy, distillation, and recrystallization
You can also.

(Production Method G) (In the compound of the present invention, R
Method for producing compound wherein ⁶ is T ⁴ , T ⁵ or T ⁷ ) Formula (17) (Wherein, J and R ¹⁵ have the same meanings as described above, and L ¹ represents a chlorine atom or a bromine atom.) [In the case of producing a compound of the present invention wherein R ⁶ is T ⁴ Or equation (18) (Wherein, R ¹⁵ has the same meaning as described above) [in the case of producing a compound of the present invention in which R ⁶ is T ⁴ and J is an oxygen atom], or Equation (1
9) (Wherein J, R ¹⁶ , R ¹⁷ and L ¹ have the same meanings as described above) (in the case of producing a compound of the present invention wherein R ⁶ is T ⁵ ); (2
0) (Wherein R ¹⁸ and L ¹ represent the same meaning as described above) (in the case of producing a compound of the present invention wherein R ⁶ is T ⁷ ) and the above-mentioned formula (16) A method of reacting with a compound represented by the formula: The reaction is performed in an inert solvent in the presence of a suitable base. As the solvent, ketones such as acetone, methyl ethyl ketone and cyclohexanone, 1,2-dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (for example, C ₁
-C ₄₎ ether (e.g., ethers such as diethyl ether, diisopropyl ether, etc.), N, N- dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile, polar solvents such as nitromethane, dichloromethane, chloroform, Examples include halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, and hydrocarbons such as toluene, benzene, and xylene, and a mixed solvent of these solvents can also be used. As the base, lithium hydroxide,
Alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal or alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate, hydrogen Alkali metal or alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide (for example, C ₁ -C ₄ ), organic bases such as triethylamine and pyridine, and the like, and it is preferable to use organic bases such as triethylamine and pyridine. The reaction temperature can usually range from -20 ° C to the boiling point of the solvent used in the reaction or 150 ° C, but more preferably from -5 ° C to the boiling point of the solvent used in the reaction or 50 ° C. The molar ratio of the starting material and the base to be subjected to the reaction can be arbitrarily set, but the formula (1)
The reaction is carried out using 1 to 5 mol of the compound represented by the formula (17), (18), (19) or (20) and 1 mol of the base per 1 mol of the compound represented by 6). Is advantageous. After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production method H) (R ^{6 in the} compound of the present invention)
And There preparation of compounds that are T ⁶⁾ formula ^{(21) R 16 -N = C} = J ( wherein, an isocyanate compound J and R ¹⁶ are represented by the representative.) As defined above or isothiocyanate compound, A method of reacting the compound represented by the formula (16). The reaction is carried out in an inert solvent, if necessary, in the presence of a suitable catalyst. As the solvent, acetone, methyl ethyl ketone, ketones such as cyclohexanone, 1,2-dimethoxyethane, tetrahydrofuran,
Ethers such as dioxane, dialkyl (for example, C ₁ -C ₄ ) ether (for example, diethyl ether, diisopropyl ether, etc.), N, N-dimethylformamide,
Polar solvents such as dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; and hydrocarbons such as toluene, benzene and xylene. And mixed solvents of these solvents can also be used. As the catalyst, for example, a base such as triethylamine, pyridine, and sodium acetate, or an acid such as aluminum chloride, hydrogen chloride, and boron trifluoride ether complex (BF _3. (C ₂ H ₅ ) ₂ O) can be used. . The reaction temperature can usually range from -20 ° C to the boiling point of the solvent used in the reaction, more preferably from -5 ° C to the boiling point of the solvent used in the reaction. The molar ratio of the raw materials to be used for the reaction can be arbitrarily set, but the reaction is desirably carried out at an equimolar ratio or a ratio close thereto. After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration to isolate the target compound of the present invention.
The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production Method I) (In the compound of the present invention, R
Method for producing compound in which ⁶ is a tert-butyl group) Isobutene (CH ₂ ＣC (CH ₃ ) ₂ ) and the above formula (16)
A method of reacting with a compound represented by the formula: The reaction is performed in an inert solvent in the presence of an acid catalyst. As the solvent, for example, hydrocarbons such as toluene, benzene, xylene,
Halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene;
- dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (eg C ₁ -C ₄₎ ether (e.g.,
Ethers such as diethyl ether and diisopropyl ether); esters such as ethyl acetate; and a mixed solvent of these solvents can also be used. Examples of the acid catalyst include inorganic acids such as hydrochloric acid, hydrobromic acid, perchloric acid, sulfuric acid, nitric acid, and phosphoric acid, or trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and benzenesulfonic acid. And organic acids such as p-toluenesulfonic acid and camphorsulfonic acid. The reaction temperature can range from −50 ° C. to 50 ° C. or the boiling point of the solvent used in the reaction. The molar ratio of the raw materials to be used for the reaction can be arbitrarily set, but it is preferable to perform the reaction using 1 mol or more of isobutene per 1 mol of the compound represented by the formula (16). After completion of the reaction, the reaction solution is subjected to ordinary post-treatment operations such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

When the compound of the present invention is a compound having an asymmetric carbon atom, the compound of the present invention is a biologically active optically active isomer ((+)-isomer, (-)-isomer) and any ratio thereof. When the compound of the present invention is a compound having geometric isomerism, the compound of the present invention includes each geometric isomer having biological activity (cis-isomer, trans-isomer) and a mixture thereof in any ratio.

Next, specific examples of the compound of the present invention are shown in Chemical formula 1, but the compound of the present invention is not limited thereto.

Embedded image (Chemical 1-1)

(Chemical 1-2)

(Formula 1-3)

(Chemical 1-4)

(Formula 1-5)

(Formula 1-6)

(Formula 1-7)

(Formula 1-8)

(Formula 1-9)

(Formula 1-10)

(Formula 1-11)

(Formula 1-12)

(Formula 1-13)

(Formula 1-14)

(Formula 1-15)

(Formula 1-16)

(Formula 1-17)

(Formula 1-18)

(Formula 1-19)

(Formula 1-20)

(Formula 1-21)

(Formula 1-22)

(Formula 1-23)

(Formula 1-24)

(Formula 1-25)

(Formula 1-26)

(Formula 1-27)

(Formula 1-28)

(Formula 1-29)

(Formula 1-30)

(Formula 1-31)

(Formula 1-32)

(Formula 1-33)

(Formula 1-34)

(Formula 1-35)

(Formula 1-36)

(Formula 1-37)

(Formula 1-38)

(Formula 1-39)

(Formula 1-40)

(Formula 1-41)

(Formula 1-42)

(Formula 1-43)

(Formula 1-44)

(Formula 1-45)

(Formula 1-46)

(Formula 1-47)

(Formula 1-48)

(Formula 1-49)

(Formula 1-50)

(Formula 1-51)

(Formula 1-52)

(Formula 1-53)

(Formula 1-54)

(Formula 1-55)

(Formula 1-56)

(Formula 1-57)

(Formula 1-58)

(Formula 1-59)

(Formula 1-60)

(Formula 1-61)

(Formula 1-62)

(Formula 1-63)

(Formula 1-64)

(Formula 1-65)

(Formula 1-66)

(Formula 1-67)

(Formula 1-68)

(Formula 1-69)

(Formula 1-70)

(Formula 1-71)

(Formula 1-72)

(Formula 1-73)

(Formula 1-74)

(Formula 1-75)

(Formula 1-76)

(Formula 1-77) In {of ^1, (R 1) _a, as the R ^2, R ³ and M _2, for example, those illustrated in Table 1 below are exemplified, R ⁶
Examples thereof include those exemplified in Tables 2 to 18 below. ｝

[0097]

[Table 1] (Table 1-1) (R ¹ ) _a R ² R ³ M ₂ ――――――――――――――――――――――――――――― _{----- H Cl Cl Cl 2 H Cl} Cl Br 2 H Cl Cl F 2 H Cl Cl Cl, F H Cl Cl Cl, Br H Cl Cl F, Br H Cl F Cl 2 H Cl F Br 2 H Cl _{F F 2 H Cl F Cl,} F H Cl F Cl, Br H Cl F F, Br H Cl Br Cl 2 H Cl Br Br 2 H Cl Br F 2 H Cl Br Cl, F H Cl Br Cl, Br H Cl _{Br F, Br H Cl CF 3} Cl 2 H Cl CF 3 Br 2 H Cl CF 3 F 2 H Cl CF 3 Cl, F H Cl CF 3 Cl, Br

(Table 1-2) (R ¹ ) _a R ² R ³ M ₂ ―――――――――――――――――――――――――――――― _{---- H Cl CF 3 F, Br} H Cl CH 3 Cl 2 H Cl CH 3 Br 2 H Cl CH 3 F 2 H Cl CH 3 Cl, F H Cl CH 3 Cl, Br H Cl CH 3 F, Br _{H Cl CH 3 CH 2 Cl 2} H Cl CH 3 CH 2 Br 2 H Cl CH 3 CH 2 F 2 H Cl CH 3 CH 2 Cl, F H Cl CH 3 CH 2 Cl, Br H Cl CH 3 CH 2 F, _{Br H Cl CH 3 CH 2 CH} 2 Cl 2 H Cl CH 3 CH 2 CH 2 Br 2 H Cl CH 3 CH 2 CH 2 Cl, F H Cl CH 3 CH 2 CH 2 Cl, Br H Cl CH 3 CH 2 CH _{2 F, Br H Cl (CH} 3) 2 CH Cl 2 H Cl (CH 3) 2 CH Br 2 H Cl (CH 3) ₂ CH Cl, F HCl (CH ₃ ) ₂ CH Cl, Br HCl (CH ₃ ) ₂ CH F, Br H F F Cl ₂

(Table 1-3) (R ¹ ) _a R ² R ³ M ₂ ―――――――――――――――――――――――――――――― _{---- H F F Br 2 H F} Br Cl 2 H F Br Br 2 H F CF 3 Cl 2 H F CF 3 Br 2 H F CH 3 Cl 2 H F CH 3 Br 2 H F CH 3 CH 2 Cl _{2 H F CH 3 CH 2 Br} 2 H F CH 3 CH 2 CH 2 Cl 2 H F CH 3 CH 2 CH 2 Br 2 H F (CH 3) 2 CH Cl 2 H F (CH 3) 2 CH Br 2 H _{Br Br Cl 2 H Br Br Br} 2 H Br CF 3 Cl 2 H Br CF 3 Br 2 H Br CH 3 Cl 2 H Br CH 3 Br 2 H Br CH 3 CH 2 Cl 2 H Br CH 3 CH 2 Br 2 H _{Br CH 3 CH 2 CH 2 Cl} 2 H Br CH 3 CH 2 CH 2 Br 2 H Br (CH 3) 2 CH Cl 2

(Table 1-4) (R ¹ ) _a R ² R ³ M ₂ ―――――――――――――――――――――――――――――― _{---- H Br (CH 3) 2} CH Br 2 H CH 3 CF 3 Cl 2 H CH 3 CF 3 Br 2 H CH 3 CH 3 Cl 2 H CH 3 CH 3 Br 2 H CH 3 CH 3 CH 2 Cl _{2 H CH 3 CH 3 CH 2} Br 2 H CH 3 CH 3 CH 2 F 2 H CH 3 CH 3 CH 2 Cl, F H CH 3 CH 3 CH 2 Cl, Br H CH 3 CH 3 CH 2 F, Br H _{CH 3 CH 3 CH 2 CH 2} Cl 2 H CH 3 CH 3 CH 2 CH 2 Br 2 H CH 3 (CH 3) 2 CH Cl 2 H CH 3 (CH 3) 2 CH Br 2 H CH 3 CH 2 CF 3 _{Cl 2 H CH 3 CH 2 CF} 3 Br 2 H CH 3 CH 2 CH 3 CH 2 Cl 2 H CH 3 CH 2 CH 3 CH 2 Br 2 H CH 3 CH 2 CH 3 C _{2 F 2 H CH 3 CH 2} CH 3 CH 2 Cl, F H CH 3 CH 2 CH 3 CH 2 Cl, Br H CH 3 CH 2 CH 3 CH 2 F, Br H CH 3 CH 2 CH 3 CH 2 CH 2 Cl ₂

(Table 1-5) (R ¹ ) _a R ² R ³ M ₂ ―――――――――――――――――――――――――――――― _{---- H CH 3 CH 2 CH 3} CH 2 CH 2 Br 2 H CH 3 CH 2 (CH 3) 2 CH Cl 2 H CH 3 CH 2 (CH 3) 2 CH Br 2 H CH 3 CH 2 CH 2 _{CF 3 Cl 2 H CH 3 CH} 2 CH 2 CF 3 Br 2 H CH 3 CH 2 CH 2 CH 3 CH 2 CH 2 Cl 2 H CH 3 CH 2 CH 2 CH 3 CH 2 CH 2 Br 2 H CH 3 CH 2 _{CH 2 (CH 3) 2 CH} Cl 2 H CH 3 CH 2 CH 2 (CH 3) 2 CH Br 2 H (CH 3) 2 CH CF 3 Cl 2 H (CH 3) 2 CH CF 3 Br 2 H (CH _{3) 2 CH (CH 3)} 2 CH Cl 2 H (CH 3) 2 CH (CH 3) 2 CH Br 2 H CF 3 CF 3 Cl 2 H CF 3 CF 3 Br 2 H OC _{3 OCH 3 Cl 2 H OCH 3} OCH 3 Br 2 2-F Cl Cl Cl 2 2-F Cl Cl Br 2 2-F Cl CH 3 Cl 2 2-F CH 3 CH 2 CH 3 CH 2 Cl 2 2-F CH ₃ CH ₂ CH ₃ CH ₂ Br ₂ 2-F CH ₃ CH ₂ CH ₃ Cl ₂ 2-F CH ₃ CH ₂ CH ₃ Br ₂

(Table 1-6) (R ¹ ) _a R ² R ³ M ₂ ―――――――――――――――――――――――――――――― --- 2-Cl Cl Cl Cl ₂ 2-Cl Cl Cl Br 22 ₂ -Cl Cl CH ₃ Cl ₂ 2-Cl CH ₃ CH ₂ CH ₃ CH ₂ Cl ₂ 2-Cl CH ₃ CH ₂ CH ₃ CH ₂ Br ₂ 2-Cl CH ₃ CH ₂ CH ₃ Cl ₂ 2-Cl CH ₃ CH ₂ CH ₃ Br ₂ 2-Br Cl Cl Cl ₂ 2-Br CH ₃ CH ₂ CH ₃ CH ₂ Cl ₂ 2-Br CH ₃ CH ₂ CH ₃ Cl ₂ 2-CH ₃ Cl Cl Cl ₂ 2-CH ₃ CH ₃ CH ₂ CH ₃ CH ₂ Cl ₂ 2-CH ₃ CH ₃ CH ₂ CH ₃ Cl ₂ 2,6-Cl ₂ Cl Cl Cl ₂ 2 _{, 6-Cl 2 CH 3 CH} 2 CH 3 CH 2 Cl 2 2,6-Cl 2 CH 3 CH 2 CH 3 Cl 2 2-C 2 H 5 Cl Cl Cl 2 _{-C 2 H 5 CH 3 CH 2} CH 3 CH 2 Cl 2 2-C 2 H 5 CH 3 CH 2 CH 3 Cl 2 2-n-C 3 H 7 Cl Cl Cl 2 2-n-C 3 H 7 CH _{3 CH 2 CH 3 CH 2 Cl} 2 2-n-C 3 H 7 CH 3 CH 2 CH 3 Cl 2

[0103]

Table 2 (Table 2-1) R ⁶ - ─────────────────────────────────── H- _{CH 3 - CH 3 CH 2 -} CH 3 CH 2 CH 2 - (CH 3) 2 CHCH 3 CH 2 CH 2 CH 2 - (CH 3) 2 CHCH 2 - CH 3 CH 2 CH (CH 3) - ( CH ₃ ) ₃ C—CH ₃ CH ₂ CH ₂ CH ₂ CH ₂ — (CH ₃ ) ₂ CHCH ₂ CH ₂ —CH ₃ CH ₂ CH (CH ₃ ) CH ₂ — (CH ₃ ) ₃ CCH ₂ —CH ₃ CH _{2 CH 2 CH (CH 3)} - (CH 3) 2 CHCH (CH 3) - CH 3 CH 2 C (CH 3) 2 - (CH 3 CH 2) 2 CHCH 3 CH 2 CH 2 CH 2 CH 2 _{CH 2 - CH 3 CH 2 CH} 2 CH 2 CH (CH 3) - CH 3 CH 2 CH 2 CH (CH 2 CH 3) - CH 3 CH 2 CH 2 C (CH 3) 2 - (CH 3 ) ₂ CHC (CH ₃ ) _2- (CH ₃ CH ₂ ) ₂ C (CH ₃ )-

(Table 2-2) R ⁶ —───────────────────────────────────CH ₃ CH _{2 CH 2 CH 2 CH 2 CH} 2 CH 2 - CH 3 CH 2 CH 2 CH 2 CH 2 CH (CH 3) - CH 3 CH 2 CH 2 CH 2 CH (CH 2 CH 3) - (CH 3 CH 2 CH _{2) 2 CH- CH 3 CH 2} CH 2 CH 2 C (CH 3) 2 - (CH 3) 3 CC (CH 3) 2 - CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 - CH _{3 CH 2 CH 2 CH 2 CH} 2 C (CH 3) 2 - (CH 3) 3 CCH 2 C (CH 3) 2 - CH 2 = CHCH 2 - CH 3 CH = CHCH 2 - CH 2 = C (CH 3 _{) CH 2 - CH 2 = CHCH} (CH 3) - (CH 3) 2 C = CHCH 2 - CH 3 CH 2 CH = CHCH 2 - CH 3 CH 2 CH 2 CH = CH _{CH 2 - (CH 3) 2} CHCH = CHCH 2 - CH 2 = C (CH 2 CH 3) CH 2 - CH 2 = C (CH 2 CH 2 CH 3) CH 2 - CH 2 = C (CH (CH 3 _{) 2) CH 2 - CH 2} = CHCH (CH 2 CH 3) - CH 2 = CHCH (CH 2 CH 2 CH 3) - CH 2 = CHCH (CH (CH 3) 2) - CH 2 = CHCH 2 CH 2 −

(Table 2-3) R ⁶ -───────────────────────────────────CH ₂ = CHCH ₂ CH ₂ CH ₂ —CH ₂ ＣＨCHCH ₂ CH ₂ CH ₂ CH ₂ — (CH ₃ ) ₂ C = CHCH ₂ CH ₂ —HC≡CCH ₂ —CH ₃ C≡CCH ₂ —HC≡CCH (CH ₃ ) -HC≡CCH ₂ CH ₂ -CH ₃ C≡CCH ₂ CH ₂ -HC≡CCH ₂ CH (CH ₃ ) -CH ₃ CH ₂ C≡CCH ₂ -HC≡CCH (CH ₂ CH ₃ ) -HC≡CCH _{2 CH 2 CH 2 - HC≡CCH 2 CH} 2 CH 2 CH 2 - CH 2 FCH 2 - CHF 2 CH 2 - CF 3 CH 2 - CH 2 ClCH 2 - CHCl 2 CH 2 - CCl 3 CH 2 - CH 2 BrCH 2 _{- CH 2 ICH 2 - CHBr 2} CH 2 - CBr 3 CH 2 - CFCl 2 CH 2 -

(Table 2-4) R ⁶ -───────────────────────────────────CFBr ₂ CH _{2 - BrCF 2 CF 2 - CHF} 2 CF 2 - CHFClCF 2 - CH 2 FCH 2 CH 2 - CHF 2 CH 2 CH 2 - CF 3 CH 2 CH 2 - CH 2 ClCH 2 CH 2 - CHCl 2 CH 2 CH 2 - CCl ₃ CH ₂ CH ₂ —CH ₂ BrCH ₂ CH ₂ —CH ₂ ICH ₂ CH ₂ —CHBr ₂ CH ₂ CH ₂ —CBr ₃ CH ₂ CH ₂ —CF ₃ CF ₂ CH ₂ —CHF ₂ CF ₂ CH ₂ —CH _{3 CHFCH 2 - CF 3 CHF 2} CF 2 - CH 3 CHClCH 2 - CH 3 CHBrCH 2 - CH 2 ClCHClCH 2 - CH 2 BrCHBrCH 2 - CH 2 FCH (CH 3) - CH 2 ClCH (CH 3) -

(Table 2-5) R ⁶ —───────────────────────────────────CH ₂ BrCH _{(CH 3) - (CH 2} F) 2 CH- (CH 2 Cl) 2 CH- (CH 2 Br) 2 CH- CF 3 CH (CH 3) - CH 2 FCH 2 CH 2 CH 2 - CH 2 ClCH 2 _{CH 2 CH 2 - CH 2 BrCH} 2 CH 2 CH 2 - CH 3 CHClCH 2 CH 2 - CH 3 CHBrCH 2 CH 2 - CH 2 ClCHClCH 2 CH 2 - CH 2 BrCHBrCH 2 CH 2 - CF 3 CF 2 CF 2 CH 2 _{- CF 3 CF 2 CH 2 CH} 2 - CF 3 CHFCF 2 CH 2 - CHF 2 CF 2 CF 2 CH 2 - CF 3 CH 2 CH 2 CH 2 - CH 2 ClCHClCHClCH 2 - CBrF 2 CF 2 CH 2 CH 2 - CH _{2 ClCH 2 CH (CH 3)} - C _{2 BrCH 2 CH (CH 3)} - CH 3 CHClCH (CH 3) - CH 3 CHBrCH (CH 3) - (CH 3) 2 CClCH 2 -

(Table 2-6) R ⁶ -─────────────────────────────────── (CH _{3 ) 2 CBrCH 2 - CH 3 CH} 2 CHClCH 2 - CH 3 CH 2 CHBrCH 2 - CH 2 FCH 2 CH 2 CH 2 CH 2 - CH 2 ClCH 2 CH 2 CH 2 CH 2 - CH 2 BrCH 2 CH 2 CH 2 CH _{2 - CH 3 CHClCH 2 CH 2} CH 2 - CH 3 CHBrCH 2 CH 2 CH 2 - CH 3 C (CH 2 Cl) 2 CH 2 - CH 3 C (CH 2 Br) 2 CH 2 - CF 3 CF 2 CF 2 _{CF 2 CH 2 - CF 3 CH} 2 CH 2 CH 2 CH 2 - CH 2 FCH 2 CH 2 CH 2 CH 2 CH 2 - CH 2 ClCH 2 CH 2 CH 2 CH 2 CH 2 - CH 2 BrCH 2 CH 2 CH 2 _{CH 2 CH 2 - C (CH} 3) 3 CHClCH 2 - C (CH 3) 3 _{HBrCH 2 - CF 3 CF 2 CF} 2 CF 2 CF 2 CH 2 - CF 3 CH 2 CH 2 CH 2 CH 2 CH 2 - CHCl = CHCH 2 - CH 3 CCl = CHCH 2 - CH 3 CH 2 CCl = CHCH 2 - _{CH 3 CH 2 CH 2 CCl =} CHCH 2 - CH (CH 3) 2 CCl = CHCH 2 -

(Table 2-7) R ⁶ —───────────────────────────────────CF ₃ CCl _{= CHCH 2 - CClF 2 CCl =} CHCH 2 - CBrF 2 CCl = CHCH 2 - CF 3 CF 2 CCl = CHCH 2 - CF 3 CF 2 CF 2 CCl = CHCH 2 - CHCl = C (CH 3) CH 2 - CH 3 _{CCl = C (CH 3) CH} 2 - CH 3 CH 2 CCl = C (CH 3) CH 2 - CF 3 CCl = C (CH 3) CH 2 - CF 3 CF 2 CCl = C (CH 3) CH 2 - _{CHCl = C (CH 2 CH 3} ) CH 2 - CH 3 CCl = C (CH 2 CH 3) CH 2 - CF 3 CCl = C (CH 2 CH 3) CH 2 - CHCl = C (CH 2 CH 2 CH 3 _{) CH 2 - CHCl = C (} CH (CH 3) 2) CH 2 - CHCl = C (CF 3) CH ₂ —CH ₃ CCl ＝ C (CF ₃ ) CH ₂ —CF ₃ CCl ＝ C (CF ₃ ) CH ₂ —CH ₂ ＣCClCH ₂ —CH ₃ CH ＝ CClCH ₂ —CH ₃ CH ₂ CH ＝ CClCH ₂ —CH _{3 CH 2 CH 2 CH = CClCH} 2 - CH (CH 3) 2 CH = CClCH 2 - CH 3 CH 2 C (CH 3) = CClCH 2 -

(Table 2-8) R ⁶ −─────────────────────────────────── CHBr = CHCH _{2 - CH 3 CBr = CHCH 2} - CH 3 CH 2 CBr = CHCH 2 - CH 3 CH 2 CH 2 CBr = CHCH 2 - CH (CH 3) 2 CBr = CHCH 2 - CF 3 CBr = CHCH 2 - CF 3 CF ₂ CBr = CHCH ₂ —CHBr = C (CH ₃ ) CH ₂ —CH ₃ CBr = C (CH ₃ ) CH ₂ —CH ₃ CH ₂ CBr = C (CH ₃ ) CH ₂ —CF ₃ CBr = C (CH _{3 ) CH 2 - CF 3 CF 2} CBr = C (CH 3) CH 2 - CHBr = C (CH 2 CH 3) CH 2 - CH 3 CBr = C (CH 2 CH 3) CH 2 - CF 3 CBr = C ( _{CH 2 CH 3) CH 2 -} CHBr = C (CH 2 CH 2 CH 3) CH 2 - CH _{r = C (CH (CH 3} ) 2) CH 2 - CH 2 = CBrCH 2 - CH 3 CH = CBrCH 2 - CH 3 CH 2 CH = CBrCH 2 - CH 3 CH 2 CH 2 CH = CBrCH 2 - CH (CH ₃ ) ₂ CH = CBrCH ₂ —CH ₃ CH ₂ C (CH ₃ ) = CBrCH ₂ —CHF = CHCH ₂ —

(Table 2-9) R ⁶ —───────────────────────────────────CH ₃ CF _{= CHCH 2 - CH 3 CH 2} CF = CHCH 2 - CH 3 CH 2 CH 2 CF = CHCH 2 - CH (CH 3) 2 CF = CHCH 2 - CF 3 CF = CHCH 2 - CF 3 CF 2 CF 2 CF = _{CHCH 2 - CHF = C (CH} 3) CH 2 - CH 3 CF = C (CH 3) CH 2 - CH 3 CH 2 CF = C (CH 3) CH 2 - CF 3 CF = C (CH 3) CH 2 _{- CF 3 CF 2 CF = C} (CH 3) CH 2 - CHF = C (CH 2 CH 3) CH 2 - CH 3 CF = C (CH 2 CH 3) CH 2 - CF 3 CF = C (CH 2 CH _{3) CH 2 - CHF = C} (CH 2 CH 2 CH 3) CH 2 - CHF = C (CH (CH 3) 2) CH 2 - CH 2 = CF _{H 2 - CH 3 CH = CFCH} 2 - CH 3 CH 2 CH = CFCH 2 - CH 3 CH 2 CH 2 CH = CFCH 2 - CH (CH 3) 2 CH = CFCH 2 - CH 3 CH 2 C (CH 3) _{= CFCH 2 - CCl 2 = CHCH} 2 - CCl 2 = C (CH 3) CH 2 -

(Table 2-10) R ⁶ −───────────────────────────────────CCl ₂ = C (CH ₂ CH ₃ ) CH ₂ —CCl ₂ ＣＨC (CH ₂ CH ₂ CH ₃ ) CH ₂ —CCl ₂ 3C (CH (CH ₃ ) ₂ ) CH ₂ —CCl ₂ ＣC (CF ₃ ) CH _{2 - CBr 2 = CHCH 2 - CBr} 2 = C (CH 3) CH 2 - CBr 2 = C (CH 2 CH 3) CH 2 - CBr 2 = C (CH 2 CH 2 CH 3) CH 2 - CBr 2 = C _{(CH (CH 3) 2)} CH 2 - CBr 2 = C (CF 3) CH 2 - CF 2 = CHCH 2 - CF 2 = C (CH 3) CH 2 - CF 2 = C (CH 2 CH 3) CH _{2 - CF 2 = C (CH} 2 CH 2 CH 3) CH 2 - CF 2 = C (CH (CH 3) 2) CH 2 - CF 2 = C (CF 3) CH 2 - CClBr = C _{CH 2 - CClF = CHCH 2 -} CBrF = CHCH 2 - CHCl = CClCH 2 - CH 3 CCl = CClCH 2 - CH 3 CH 2 CCl = CClCH 2 - CH 3 CH 2 CH 2 CCl = CClCH 2 - CH (CH 3) ₂ CCl = CClCH ₂ −

(Table 2-11) R ⁶ −─────────────────────────────────── CHBr = CBrCH _{2 - CH 3 CBr = CBrCH 2} - CH 3 CH 2 CBr = CBrCH 2 - CH 3 CH 2 CH 2 CBr = CBrCH 2 - CH (CH 3) 2 CBr = CBrCH 2 - CCl 2 = CClCH 2 - CBr 2 = CBrCH _{2 - CF 3 CH = CHCH 2} - CF 3 C (CH 3) = CHCH 2 - (CF 3) 2 C = CHCH 2 - CF 3 CH = C (CH 3) CH 2 - CH 2 = C (CF 3) _{CH 2 - CHCl = CHCH 2 CH} 2 - CH 3 CCl = CHCH 2 CH 2 - CH 3 CH 2 CCl = CHCH 2 CH 2 - CF 3 CCl = CHCH 2 CH 2 - CF 3 CF 2 CCl = CHCH 2 CH 2 - CHCl = C (CH ₃ ) CH _{2 CH 2 - CH 3 CCl =} C (CH 3) CH 2 CH 2 - CF 3 CCl = C (CH 3) CH 2 CH 2 - CHCl = C (CH 2 CH 3) CH 2 CH 2 - CH 2 = CClCH _{2 CH 2 - CH 3 CH =} CClCH 2 CH 2 - CH 3 CH 2 CH = CClCH 2 CH 2 -

(Table 2-12) R ⁶ —───────────────────────────────────CHBr = CHCH _{2 CH 2 - CH 3 CBr =} CHCH 2 CH 2 - CH 3 CH 2 CBr = CHCH 2 CH 2 - CF 3 CBr = CHCH 2 CH 2 - CF 3 CF 2 CBr = CHCH 2 CH 2 - CHBr = C (CH 3 _{) CH 2 CH 2 - CH 3} CBr = C (CH 3) CH 2 CH 2 - CF 3 CBr = C (CH 3) CH 2 CH 2 - CHBr = C (CH 2 CH 3) CH 2 CH 2 - CH 2 _{= CBrCH 2 CH 2 - CH 3} CH 2 = CBrCH 2 CH 2 - CH 3 CH 2 CH = CBrCH 2 CH 2 - CHF = CHCH 2 CH 2 - CH 3 CF = CHCH 2 CH 2 - CH 3 CH 2 CF = CHCH _{2 CH 2 - CF 3 CF =} CHCH 2 CH 2 - C _{3 CF 2 CF = CHCH 2 CH} 2 - CHF = C (CH 3) CH 2 CH 2 - CH 3 CF = C (CH 3) CH 2 CH 2 - CF 3 CF = C (CH 3) CH 2 CH 2 - _{CHF = C (CH 2 CH 3} ) CH 2 CH 2 - CH 2 = CFCH 2 CH 2 - CH 3 CH = CFCH 2 CH 2 - CH 3 CH 2 CH = CFCH 2 CH 2 -

(Table 2-13) R ⁶ −───────────────────────────────────CCl ₂ = _{CHCH 2 CH 2 - CCl 2 =} C (CH 3) CH 2 CH 2 - CCl 2 = C (CH 2 CH 3) CH 2 CH 2 - CBr 2 = CHCH 2 CH 2 - CBr 2 = C (CH 3) CH _{2 CH 2 - CBr 2 = C} (CH 2 CH 3) CH 2 CH 2 - CF 2 = CHCH 2 CH 2 - CF 2 = C (CH 3) CH 2 CH 2 - CF 2 = C (CH 2 CH 3) _{CH 2 CH 2 - CClF = CHCH} 2 CH 2 - CClF = C (CH 3) CH 2 CH 2 - CClF = C (CH 2 CH 3) CH 2 CH 2 - CClF = C (CH 3) CH 2 CH 2 - CCIF = C (CH ₂ CH ₃ ) CH ₂ CH ₂ —CHCl = CClCH ₂ CH ₂ —CH ₃ CCl = CClCH _{2 CH 2 - CH 3 CH 2 CCl} = CClCH 2 CH 2 - CHBr = CBrCH 2 CH 2 - CH 3 CBr = CBrCH 2 CH 2 - CH 3 CH 2 CBr = CBrCH 2 CH 2 - CCl 2 = CClCH 2 CH 2 - CBr _{2 = CBrCH 2 CH 2 - CF} 3 CH = CHCH 2 CH 2 - CF 3 C (CH 3) = CHCH 2 CH 2 -

(Table 2-14) R ⁶ −─────────────────────────────────── (CF ₃ ) ₂ C = CHCH ₂ CH ₂ —CF ₃ CH = C (CH ₃ ) CH ₂ CH ₂ —CHCl = CHCH ₂ CH ₂ CH ₂ —CH ₃ CCl = CHCH ₂ CH ₂ CH ₂ —CF ₃ CCl = CHCH ₂ CH _{2 CH 2 - CHCl = C (} CH 3) CH 2 CH 2 CH 2 - CH 2 = CClCH 2 CH 2 CH 2 - CH 3 CH = CClCH 2 CH 2 CH 2 - CHBr = CHCH 2 CH 2 CH 2 - CH 3 CBr = CHCH ₂ CH ₂ CH ₂ —CF ₃ CBr = CHCH ₂ CH ₂ CH ₂ —CHBr = C (CH ₃ ) CH ₂ CH ₂ CH ₂ —CHBr = C (CF ₃ ) CH ₂ CH ₂ CH ₂ —CH ₂ ＣCBrCH ₂ CH ₂ CH ₂ —CH ₃ CHｒCBrCH ₂ CH _{2 CH 2 - CCl 2 = CHCH} 2 CH 2 CH 2 - CCl 2 = C (CH 3) CH 2 CH 2 CH 2 - CBr 2 = CHCH 2 CH 2 CH 2 - CBr 2 = C (CH 3) CH 2 CH _{2 CH 2 - CF 2 = CHCH} 2 CH 2 CH 2 - CF 2 = C (CH 3) CH 2 CH 2 CH 2 - CCl 2 = CClCH 2 CH 2 CH 2 - CBr 2 = CBrCH 2 CH 2 CH 2 - CF _{3 CH = CHCH 2 CH 2 CH} 2 -

(Table 2-15) R ⁶ -───────────────────────────────────ClC≡CCH _{2 - BrC≡CCH 2 - FC≡CCH 2 -} CF 3 C≡CCH 2 - CF 3 CF 2 C≡CCH 2 - CF 3 CF 2 CF 2 C≡CCH 2 - ClC≡CCH 2 CH 2 - BrC≡CCH 2 CH ₂ —CF ₃ C≡CCH ₂ CH ₂ —CF ₃ CF ₂ C≡CCH ₂ CH ₂ —ClC≡CCH ₂ CH ₂ CH ₂ —BrC≡CCH ₂ CH ₂ CH ₂ —CF ₃ C≡CCH ₂ CH ₂ CH ₂ - cyclopropyl cyclobutyl 1-methyl cyclobutyl group, cyclopentyl 1-methylcyclopentyl group 2-methylcyclopentyl group 3-methylcyclopentyl group cyclohexyl 1-methylcyclopropene cyclohexyl 2-methylcyclopropyl cyclo Cyclohexyl group 3-methyl dicyclohexyl group

(Table 2-16) R ⁶ -─────────────────────────────────── 4-methyl Cyclocyclohexyl group 2-ethylcyclocyclohexyl group 4-ethylcyclocyclohexyl group 2-tert-butylcyclocyclohexyl group 4-tert-butylcyclocyclohexyl group 2,3-dimethylcyclocyclohexyl group 3,4-dimethylcyclocyclohexyl group 3,5 -Dimethylcyclocyclohexyl group 2,6-dimethylcyclocyclohexyl group 3,3,5,5-tetramethylmethylcyclocyclohexyl menthyl group cycloheptyl group cyclopropylmethyl group 1-cyclopropylethyl group (1-methylcyclopropyl) methyl Group (2-methylcyclopropyl) methyl group cyclobutylmethyl Group cyclopentylmethyl group 3-cyclopentyloxy-propyl cyclohexylmethyl group 1-cyclohexyl ethyl 2-cyclohexylethyl 3-cyclohexyl-propyl 4-cyclohexyl-butyl

(Table 2-17) R ⁶ -─────────────────────────────────── 2-cyclo Pentenyl group 3-cyclopentenyl group 2-cyclohexenyl group 3-cyclohexenyl group 3-methyl-2-cyclohexenyl group 3,5,5-trimethyl-2-cyclohexenyl group (1-cyclopentenyl) methyl group (3- cyclohexenyl) methyl 2- (4-methyl-3-cyclohexenyl) propyl _{NC-CH 2 - NC-CH} (CH 3) - NC-CH 2 CH 2 - NC-CH 2 CH (CH 3) - NC _{-CH (CH 3) CH 2 -} NC-CH 2 CH 2 CH 2 NC-CH 2 CH 2 CH 2 CH 2 NO 2 -CH 2 - NO 2 -CH (CH 3) - NO 2 -C (CH 3) _{2 - CH 3 OOC-CH 2} - CH 3 OOC-C _{H (CH 3) - CH 3} OOC-C (CH 3) 2 - CH 3 OOC-CH 2 CH 2 - CH 3 OOC-CH 2 CH 2 CH 2 -

(Table 2-18) R ⁶ —───────────────────────────────────CH ₃ OOC —CH ₂ CH ₂ CH ₂ CH ₂ —CH ₃ CH ₂ OOC—CH ₂ —CH ₃ CH ₂ OOC—CH (CH ₃ ) —CH ₃ CH ₂ OOC—C (CH ₃ ) ₂ —CH ₃ CH ₂ OOC— _{CH 2 CH 2 - CH 3 CH} 2 OOC-CH 2 CH 2 CH 2 - CH 3 CH 2 OOC-CH 2 CH 2 CH 2 CH 2 - (CH 3) 2 CHOOC-CH 2 - (CH 3) 2 CHOOC- _{CH (CH 3) - (CH} 3) 2 CHOOC-C (CH 3) 2 - (CH 3) 2 CHOOC-CH 2 CH 2 - (CH 3) 2 CHOOC-CH 2 CH 2 CH 2 - (CH 3) _{2 CHOOC-CH 2 CH 2 CH} 2 CH 2 - (CH 3) 3 COOC-CH 2 - (CH 3) 3 COO _{-CH (CH 3) - (CH} 3) 3 COOC-C (CH 3) 2 - (CH 3) 3 COOC-CH 2 CH 2 - (CH 3) 3 COOC-CH 2 CH 2 CH 2 - (CH 3 ) ₃ COOC—CH ₂ CH ₂ CH ₂ CH ₂ —CH ₃ OCH ₂ —CH ₃ CH ₂ OCH ₂ —CH ₃ OCH (CH ₃ ) —CH ₃ CH ₂ OCH (CH ₃ ) —CH ₃ CH ₂ CH ₂ OCH (CH ₃₎ -

(Table 2-19) R ⁶ -─────────────────────────────────── (CH ₃ ) ₂ CHOCH (CH ₃ ) —CH ₃ CH ₂ CH ₂ CH ₂ OCH (CH ₃ ) — (CH ₃ ) ₂ CHCH ₂ OCH (CH ₃ ) —CH ₃ OC (CH ₃ ) ₂ —CH ₃ OCH ₂ CH ₂ —CH ₃ CH ₂ OCH ₂ CH ₂ — (CH ₃ ) ₂ CHOCH ₂ CH ₂ — (CH ₃ O) ₂ CHCH ₂ — (CH ₃ CH ₂ O) ₂ CHCH ₂ — (CH ₃ CH ₂ CH ₂ O) ₂ CHCH ₂ — (CH ₃ O) ₂ C (CH ₃ ) CH ₂ — (CH ₃ CH ₂ O) ₂ C (CH ₃ ) CH ₂ — (CH ₃ CH ₂ CH ₂ O) ₂ C (CH ₃ ) CH _{2 - (CH 3 O) 2 CHCH} 2 CH 2 - (CH 3 CH 2 O) 2 CHCH 2 CH 2 - (CH 3 CH 2 CH 2 O) 2 CHCH 2 CH 2 - CH ₃ SCH ₂ —CH ₃ SCH ₂ CH ₂ —CH ₃ SCH ₂ CH ₂ CH ₂ — (CH ₃ S) ₂ CHCH ₂ —triphenylmethyl group

[0122]

Table 3 R ⁶ = T ¹ (D = CH) = (Table _{^{3-1) (R 8) b -}} ─────────────────────────────────── H- 2 _{-CH 3 - 2-CH 3 CH} 2 - 2-CH 3 CH 2 CH 2 - 2- (CH 3) 2 CH- 2-CF 3 - 2-F- 2-Cl- 2-Br- 2-CH 3 _{O- 3-CH 3 - 3-} CH 3 CH 2 - 3-CH 3 CH 2 CH 2 - 3- (CH 3) 2 CH- 3-CH 3 CH 2 CH (CH 3) - 3- (CH 3) ₃ C-3-CF ₃ 3-F- 3-Cl- 3-Br-

(Table 3-2) (R ⁸ ) _b − ─────────────────────────────────── _{3-I- 3-CH 3 O-} 3-CF 3 O- 4-CH 3 - 4-CH 3 CH 2 - 4-CH 3 CH 2 CH 2 - 4- (CH 3) 2 CH- 4-CH 3 _{CH 2 CH (CH 3) -} 4- (CH 3) 3 C- 4-CH 3 CH 2 C (CH 3) 2 - 4-CF 3 - 4-F- 4-Cl- 4-Br- 4-I _{- 4-CH 3 O- 4-} CH 3 CH 2 O- 4-CH 3 CH 2 CH 2 O- 4- (CH 3) 2 CHO- 4-CH 3 CH 2 CH 2 CH 2 O- 4-CF 3 O-

[0124]

[Table 4] R ⁶ = T ¹ (D = nitrogen atom) = (Table _{^{4-1) (R 8) b -}} ─────────────────────────────────── H- 6 _{-CH 3 - 5-CH 3 -} 3-CH 3 - 4-CH 3 - 6-Cl- 5-Cl- 6-Br- 5-Br- 6-CF 3 - 5-CF 3 - 5-NO 2 - 4,6- (CH ₃ ) ₂ -3,5- (CF ₃ ) ₂ -3,5-Cl ₂ -3-F—, 5-CF ₃ -3-Cl—, 5-CF ₃ -3-Br _{-, 5-CF 3 - 3} -NO 2 -, 5-Br- 3-NO 2 -, 4-CH 3 -

(Table 4-2) (R ⁸ ) _b − ─────────────────────────────────── _{4-CH 3 -, 5-} NO 2 - 3,5,6-F 3 - 3,5,6-F 3 -, 4-CH 3 - 3,5,6-F 3 -, 4-Br- 3 _{, 4,5,6-F 4 - 3,4,5,6-} Cl 4 - 3,5-Cl 2 -, 4,6-F 2 -,

[0126]

[Table 5] R ⁶ = T ¹ (D = nitrogen atom) = _{^{(R 8) b - ─────────────────────────────────── H-}} 6-CH 3 - 2- _{CH 3 - 5-Cl- 2-} Cl- 2-Br- 2-I-, 6-CH 3 -

[0127]

[Table 6] R ⁶ = T ¹ (D = nitrogen atom) = (R ⁸ ) _b -───────────────────────────────────H-2,6-F ₂

[0128]

Table 7 R ⁶ = T ² (D = CH) = (Table 7-1) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d − ───────────────────────────── _{────── H- -CH 2 - 2-F-} -CH 2 - 3-F- -CH 2 - 4-F- -CH 2 - 2-Cl- -CH 2 - 3-Cl- -CH _{2 - 4-Cl- -CH 2 -} 2-Br- -CH 2 - 3-Br- -CH 2 - 4-Br- -CH 2 - 2-I- -CH 2 - 3-I- -CH 2 - _{4-I- -CH 2 - 2-} CH 3 - -CH 2 - 3-CH 3 - -CH 2 - 4-CH 3 - -CH 2 - 4-CH 3 CH 2 - -CH 2 - 4-CH 3 _{CH 2 CH 2 - -CH 2 -} 4- (CH 3) 2 CH- -CH 2 - 4-CH 3 CH 2 CH 2 CH 2 - -CH 2 -

(Table 7-2) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d −────────────────────────── _{───────── 4- (CH 3) 3 C-} -CH 2 - 2-CF 3 - -CH 2 - 3-CF 3 - -CH 2 - 4-CF 3 - -CH 2 - 2 _{-CH 3 O- -CH 2 - 3-} CH 3 O- -CH 2 - 4-CH 3 O- -CH 2 - 2-CH 3 CH 2 O- -CH 2 - 3-CH 3 CH 2 O- - _{CH 2 - 4-CH 3 CH} 2 O- -CH 2 - 4-CH 3 CH 2 CH 2 O- -CH 2 - 4- (CH 3) 2 CH-O- -CH 2 - 4-CH 3 CH 2 _{CH 2 CH 2 O- -CH 2 -} 4- (CH 3) 3 CO- -CH 2 - 2-CF 3 O- -CH 2 - 3-CF 3 O- -CH 2 - 4-CF 3 O- - CH _2-4 -CH ₃ OOC——CH ₂ 2-NO _{2 - -CH 2 - 3-NO} 2 - -CH 2 - 4-NO 2 - -CH 2 - 2-CN- -CH 2 - 3-CN- -CH 2 - 4-CN- -CH 2 -

(Table 7-3) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d −────────────────────────── _{───────── 2,3-F 2 - -CH 2} - 2,4-F 2 - -CH 2 - 2,5-F 2 - -CH 2 - 2,6-F 2 - - _{CH 2 - 3,4-F 2 -} -CH 2 - 3,5-F 2 - -CH 2 - 2,3-Cl 2 - -CH 2 - 2,4-Cl 2 - -CH 2 - 2,5 _{-Cl 2 - -CH 2 - 2,6-} Cl 2 - -CH 2 - 3,4-Cl 2 - -CH 2 - 3,5-Cl 2 - -CH 2 - 2,5-Br 2 - -CH _{2 - 3,5-Br 2 - -CH} 2 - 2-F-, 4-Cl- -CH 2 - 2-Cl-, 4-F- -CH 2 - 2-Cl-, 6-F- -CH _{2 - 3-Cl-, 4-} F- -CH 2 - 2-F-, 4-Br- -CH 2 - 2-F- _{5-Br- -CH 2 - 2-} Br-, 4-F- -CH 2 - 2-Br-, 5-F- -CH 2 - 3-Br-, 4-F- -CH 2 - 2-F -, 4-I- -CH ₂ -

(Table 7-4) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d −────────────────────────── ───────── 2-Br-, 5-Cl- -CH 2 - 2,3- (CH 3) 2 - -CH 2 - 2,4- (CH 3) 2 - -CH 2 - _{2,5- (CH 3) 2 - -CH} 2 - 2,6- (CH 3) 2 - -CH 2 - 3,4- (CH 3) 2 - -CH 2 - 3,5- (CH 3) _{2 - -CH 2 - 2,4- (CF} 3) 2 - -CH 2 - 3,5- (CF 3) 2 - -CH 2 - 2-Cl-, 6-CH 3 - -CH 2 - 2- _{Br-, 6-CH 3 - -CH} 2 - 3-CH 3 -, 5-Br- -CH 2 - 2,3- (CH 3 O) 2 - -CH 2 - 2,4- (CH 3 O) _{2 - -CH 2 - 2,5- (CH} 3 O) 2 - -CH 2 - 2,6- (CH 3 O) 2 - _{-CH 2 - 3,4- (CH 3 O} ) 2 - -CH 2 - 3,5- (CH 3 O) 2 - -CH 2 - 3-CH 3 CH 2 O-, 4-CH 3 O- - _{CH 2 - 4-CH 3 CH} 2 O-, 3-CH 3 O- -CH 2 - 2-CH 3 O-, 5-Br- -CH 2 - 3,4- (NO 2) 2 - -CH 2 -3,5- (NO ₂ ) ₂ --CH ₂ -2-Cl-, 5-NO ₂ --CH _2-

(Table 7-5) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d −────────────────────────── _{───────── 2-NO 2 -, 4} -Cl- -CH 2 - 2-NO 2 -, 5-Cl- -CH 2 - 3-NO 2 -, 4-Cl- -CH 2 _{- 2-CH 3 -, 3} -NO 2 - -CH 2 - 3-CH 3 -, 4-NO 2 - -CH 2 - 2-NO 2 -, 3-CH 3 - -CH 2 - 3-NO 2 _{-, 5-CH 3 - -CH} 2 - 3-NO 2 -, 4-CH 3 - -CH 2 - 2-CH 3 O-, 5-NO 2 - -CH 2 - 3-CH 3 O-, 4 _{-NO 2 - -CH 2 - 2,3,4-} F 3 - -CH 2 - 2,4,6- (CH 3) 3 - -CH 2 - 2,3,4- (CH 3 O) 3 - _{-CH 2 - 3,4,5- (CH 3 O} ) 3 - -CH 2 - 2,3- (CH 3) 2 _{-, 4-CH 3 O- -CH} 2 - 2,4- (CH 3 O) 2, 3-CH 3 - -CH 2 - 2,3,5,6-F 4 - -CH 2 - 2,3 _{, 4,5,6-F 5 - -CH 2} - H- -CH (CH 3) - H- -CH (CH 2 CH 3) - H- -CH (CH 2 CH 2 CH 3) - H- - _{CH (CF 3) - 4-} F- -CH (CH 3) - 4-Cl- -CH (CH 3) -

(Table 7-6) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d − ────────────────────────── _{───────── 2-Br- -CH (CH 3} ) - 4-Br- -CH (CH 3) - 2-CF 3 - -CH (CH 3) - 3-CF 3 - -CH _{(CH 3) - 4-CF} 3 - -CH (CH 3) - 4-CH 3 O- -CH (CH 3) - 2,4-Cl 2 - -CH (CH 3) - 2,3,4, _{5,6-F 5 - -CH (CH} 3) - H- -CH 2 CH 2 - 2-F- -CH 2 CH 2 - 4-F- -CH 2 CH 2 - 2-Cl- -CH 2 CH _{2 - 3-Cl- -CH 2 CH} 2 - 4-Cl- -CH 2 CH 2 - 4-Br- -CH 2 CH 2 - 2-CH 3 - -CH 2 CH 2 - 3-CH 3 - -CH _{2 CH 2 - 2-CF 3} - -CH 2 CH 2 - _{-CF 3 - -CH 2 CH 2 -} 4-CH 3 - -CH 2 CH 2 - 2-CH 3 O- -CH 2 CH 2 - 3-CH 3 O- -CH 2 CH 2 - 4-CH 3 O − −CH ₂ CH ₂ − 2-NO ₂ − −CH ₂ CH ₂ −

(Table 7-7) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d − ────────────────────────── _{───────── 3-NO 2 - -CH 2} CH 2 - 4-NO 2 - -CH 2 CH 2 - 2,3- (CH 3 O) 2 - -CH 2 CH 2 - 3- in Table _{7, - - CH 3 O-,} 4-CH 3 CH 2 O- -CH 2 CH 2 - H- -CH 2 CH 2 CH 2 (CR 9 R 10) d - left bonded to the benzene ring of doing. ]

[0135]

[Table 8] R ⁶ = T ² (D = nitrogen atom) = (Table 8-1) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d − ───────────────────────────── _{────── H- -CH 2 - H- -CH 2} CH 2 - H- -CH 2 CH 2 CH 2 - H- -CH (CH 3) - 6-CH 3 - -CH 2 - 6- _{F- -CH 2 - 6-F- -CH} (CH 3) - 6-F- -CH 2 CH 2 - 6-Cl- -CH 2 - 6-Cl- -CH (CH 3) - 6-Cl- _{-CH 2 CH 2 - 5-Cl-} -CH 2 - 3-Cl- -CH 2 - 3-Cl- -CH (CH 3) - 3-Cl- -CH 2 CH 2 - 6-Br- -CH 2 _{- 6-Br- -CH (CH 3} ) - 6-Br- -CH 2 CH 2 - 5-Br- -CH 2 - 5-Br- -CH (CH 3) - 5-Br- -CH 2 CH 2 − 5-CF ₃ − −CH ₂ − 5-CF _{3 - -CH (CH 3) - 5} -CF 3 - -CH 2 CH 2 - 3,5-Cl 2 - -CH 2 -

(Table 8-2) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d −────────────────────────── _{───────── 3,5-Cl 2 - -CH (} CH 3) - 3,5-Cl 2 - -CH 2 CH 2 - 3,5- (CF 3) 2 - -CH 2 - 3,5- (CF ₃ ) ₂ ——CH (CH ₃ ) — 3,5- (CF ₃ ) ₂ ——CH ₂ CH ₂ -4,5- (CF ₃ ) ₂ ——CH ₂ -4,5 _{- (CF 3) 2 - -CH} (CH 3) - 4,5- (CF 3) 2 - -CH 2 CH 2 - 3-Cl-, 5-CF 3 - -CH 2 - 3-Cl-, 5 -CF ₃ --CH (CH ₃ ) -3-Cl-, 5-CF ₃ --CH ₂ CH _2- [In Table 8, the left side of-(CR ⁹ R ¹⁰ ) _d- is bonded to the pyridine ring. I have. ]

[0137]

[Table 9] R ⁶ = T ² (D = nitrogen atom) = (Table 9-1) (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d − ───────────────────────────── _{────── H- -CH 2 - H- -CH 2} CH 2 - H- -CH 2 CH 2 CH 2 - H- -CH (CH 3) - 6-CH 3 - -CH 2 - 6- _{CH 3 - -CH (CH 3)} - 2-CH 3 - -CH 2 - 2-CH 3 - -CH (CH 3) - 6-Cl- -CH 2 - 6-Cl- -CH (CH 3) - _{5-Cl- -CH 2 - 5-} Cl- -CH (CH 3) - 2-Cl- -CH 2 - 2-Cl- -CH (CH 3) - 6-Br- -CH 2 - 6-Br- _{-CH (CH 3) - 5-} Br- -CH 2 - 5-Br- -CH (CH 3) - 6-I- -CH 2 - 6-I- -CH (CH 3) - 5,6-Cl _{2 - -CH 2 - 5,6-Cl} 2 - -CH ( _{H 3) - 2,6-Cl 2} - -CH 2 - 2,6-Cl 2 - -CH (CH 3) - 2-Cl-, 6-CH 3 - -CH 2 - 2-Cl-, 6- CH ₃ - in Table _{9, - - -CH (CH 3} ) (CR 9 R 10) d - the left is attached to the pyridine ring. ]

[0138]

[Table 10] R ⁶ = T ² (D = nitrogen atom) = (R ⁸ ) _b − − (CR ⁹ R ¹⁰ ) _d − ─────────────────────────────────── _{H- -CH 2 - H- -CH (CH} 3) - H- -CH 2 CH 2 - H- -CH 2 CH 2 CH 2 - 2,3,5,6-F 4 - -CH 2 - Table In 10, the left side of-(CR ⁹ R ¹⁰ ) _d- is bonded to the pyridine ring. ]

[0139]

Table 11 R ⁶ = T ³ (D = CH) = (Table _{^{11-1) (R 8) b -}} - (CR 11 R 12) e -O- (CR 13 R 14) f - ─────────────────── ──────────────── H——O—CH ₂ CH ₂ —H——O—CH ₂ CH ₂ CH ₂ —H——O—CH ₂ CH ₂ CH ₂ CH _{2 - 4-F- -O-CH} 2 CH 2 CH 2 - 4-F- -O-CH 2 CH 2 CH 2 CH 2 - 4-Cl- -O-CH 2 CH 2 CH 2 - 4-Cl- _{-O-CH 2 CH 2 CH 2} CH 2 - 4-Br- -O-CH 2 CH 2 CH 2 - 4-Br- -O-CH 2 CH 2 CH 2 CH 2 - 4-CF 3 - -O- _{CH 2 CH 2 CH 2 - 4} -CF 3 - -O-CH 2 CH 2 CH 2 CH 2 - 4-CH 3 O- -O-CH 2 CH 2 CH 2 - 4-CH 3 O- -O- _{CH 2 CH 2 CH 2 CH 2} - 4-CF 3 O- _{O-CH 2 CH 2 CH 2} - 4-CF 3 O- -O-CH 2 CH 2 CH 2 CH 2 - H- -CH 2 -O-CH 2 CH 2 - H- -CH 2 -O-CH 2 _{CH 2 CH 2 - H- -CH 2} -O-CH 2 CH 2 CH 2 CH 2 - 4-F- -CH 2 -O-CH 2 CH 2 CH 2 - 4-F- -CH 2 -O-CH _{2 CH 2 CH 2 CH 2 -} 4-Cl- -CH 2 -O-CH 2 CH 2 CH 2 - 4-Cl- -CH 2 -O-CH 2 CH 2 CH 2 CH 2 - 4-Br- -CH _{2 -O-CH 2 CH 2 CH} 2 - 4-Br- -CH 2 -O-CH 2 CH 2 CH 2 CH 2 - 4-CF 3 - -CH 2 -O-CH 2 CH 2 CH 2 -

(Table 11-2) (R ⁸ ) _b --(CR ¹¹ R ¹² ) _e -O- (CR ¹³ R ¹⁴ ) _f -──────────────── _{─────────────────── 4-CF 3 - -CH 2} -O-CH 2 CH 2 CH 2 CH 2 - 4-CH 3 O- -CH 2 -O in Table _{11, - - -CH 2 CH 2} CH- 4-CH 3 O- -CH 2 -O-CH 2 CH 2 CH 2 CH 2 (CR 11 R 12) e -O- (CR 13 R 14) _f - on the left side is attached to the benzene ring. ]

[0141]

[Table 12] R ⁶ = T ³ (D = nitrogen atom) = (R ⁸ ) _b − − (CR ¹¹ R ¹² ) _e −O− (CR ¹³ R ¹⁴ ) _f − ───────────────────────── ────────── H——O—CH ₂ CH ₂ CH ₂ —H——O—CH ₂ CH ₂ CH ₂ CH ₂ —5-Cl——O—CH ₂ CH ₂ CH ₂ — 5-Cl——O—CH ₂ CH ₂ CH ₂ CH ₂ —5-Br——O—CH ₂ CH ₂ CH ₂ —5-Br——O—CH ₂ CH ₂ CH ₂ CH ₂ —5-CF ₃ ——O—CH ₂ CH ₂ CH ₂ —5-CF ₃ ——O—CH ₂ CH ₂ CH ₂ CH ₂ -3,5- (CF ₃ ) ₂ ——O—CH ₂ CH ₂ CH ₂ -3, 5- (CF ₃ ) ₂ ——O—CH ₂ CH ₂ CH ₂ CH ₂ -3,5-Cl ₂ ——O—CH ₂ CH ₂ CH ₂ -3,5-Cl ₂ ——O—CH ₂ CH _{2 CH 2 CH 2 - 3-} Cl-, 5-CF 3 - _{O-CH 2 CH 2 CH 2} - 3-Cl-, 5-CF 3 - -O-CH 2 CH 2 CH 2 CH 2 - H- -CH 2 -O-CH 2 CH 2 CH 2 - H- -CH in Table _{12, - - 2 -O-CH} 2 CH 2 CH 2 CH 2 (CR 11 R 12) e -O- (CR 13 R 14) f - left is bonded to pyridine down ring. ]

[0142]

[Table 13] R ⁶ = T ³ (D = nitrogen atom) = (R ⁸ ) _b − − (CR ¹¹ R ¹² ) _e −O− (CR ¹³ R ¹⁴ ) _f − ───────────────────────── ────────── H——O—CH ₂ CH ₂ CH ₂ —H——O—CH ₂ CH ₂ CH ₂ CH ₂ —5-Cl——O—CH ₂ CH ₂ CH ₂ — _{5-Cl- -O-CH 2 CH} 2 CH 2 CH 2 - H- -CH 2 -O-CH 2 CH 2 CH 2 - H- -CH 2 -O-CH 2 CH 2 CH 2 CH 2 - Table in ^{13, - (CR 11 R 12} ) e -O- (CR 13 R 14) f - left is bonded to pyridine down ring. ]

[0143]

Table 14 R ⁶ = T ³ (D = nitrogen atom) = (R ⁸ ) _b − − (CR ¹¹ R ¹² ) _e −O− (CR ¹³ R ¹⁴ ) _f − ───────────────────────── _{────────── H- -O-CH 2 CH 2} CH 2 - H- -O-CH 2 CH 2 CH 2 CH 2 - H- -CH 2 -O-CH 2 CH 2 CH 2 —H——CH ₂ —O—CH ₂ CH ₂ CH ₂ CH ₂ — [In Table 14, the left side of — (CR ¹¹ R ¹² ) _e —O— (CR ¹³ R ¹⁴ ) _f — is bonded to the pyridin ring. doing. ]

[0144]

Table 15 R ⁶ = T ⁴ (Table 15-1) R ⁶ −──────────────────────────────── _{─── CH 3 C (= O)} - CH 3 CH 2 C (= O) - CH 3 CH 2 CH 2 C (= O) - (CH 3) 2 CHC (= O) - CH 3 CH 2 CH 2 _{CH 2 C (= O) -} (CH 3) 2 CHCH 2 C (= O) - CH 3 CH 2 CH (CH 3) C (= O) - (CH 3) 3 CC (= O) - CH 2 = _{CHC (= O) - CH 3} CH = CHC (= O) - CH 2 = C (CH 3) C (= O) - (CH 3) 2 C = CHC (= O) - CH 2 FC (= O) _{- CHF 2 C (= O)} - CF 3 C (= O) - CH 2 ClC (= O) - CHCl 2 C (= O) - CCl 3 C (= O) - CH 2 BrC (= O) - CHBr _{2 C (= O) - CBr} 3 C (= O) -

(Table 15-2) R ⁶ -───────────────────────────────────

(Table 15-3) R ⁶ -───────────────────────────────────

[0147]

[Table 16] R ⁶ = T ⁵ R ⁶ −────────────────────────────────── (CH ₃ ) _{2 NC (= O) - (} CH 3 CH 2) 2 NC (= O) - ((CH 3) 2 CH) 2 NC (= O) -

[0148]

[Table 17] R ⁶ = T ⁶ (Table 17-1) R ⁶ −──────────────────────────────── _{── CH 3 NHC (= O)} - CH 3 CH 2 NHC (= O) - CH 3 CH 2 CH 2 NHC (= O) - (CH 3) 2 CHNHC (= O) - CH 3 CH 2 CH 2 CH _{2 NHC (= O) - (} CH 3) 3 CNHC (= O) - CH 2 = CHCH 2 NHC (= O) - CH 2 ClCH 2 NHC (= O) -

(Table 17-2) R ⁶ -──────────────────────────────────

(Table 17-3) R ⁶ —──────────────────────────────────CH ₃ NHC ( _{= S) - CH 3 CH 2} NHC (= S) - CH 3 CH 2 CH 2 NHC (= S) - (CH 3) 2 CHNHC (= S) - CH 3 CH 2 CH 2 CH 2 NHC (= S) _{- (CH 3) 3 CNHC (} = S) - CH 2 = CHCH 2 NHC (= S) -

[0151]

[Table 18] R ⁶ = T ⁷ R ⁶ −────────────────────────────────── CH ₃ S ( _{= O) 2 - CH 3 CH} 2 S (= O) 2 - CH 3 CH 2 CH 2 S (= O) 2 - (CH 3) 2 CHS (= O) 2 - CCl 3 S (= O) 2 -

Next, a method for producing an intermediate for producing the compound of the present invention will be described. Each symbol in the following schemes has the same meaning as described above unless otherwise specified. A compound represented by the formula (7), which is a production intermediate of the compound of the present invention (including a compound represented by the formula (5))
Can be produced, for example, according to Scheme 2.

[0153]

Embedded image (Scheme 2-1 except for compounds in which R ⁶ is a hydrogen atom)

(Scheme 2-2 except for a compound in which R ⁶ is a hydrogen atom)

(Scheme 2-3: Excluding compounds in which R ⁶ is a hydrogen atom)

(Scheme 2-4: except for compounds in which R ⁶ is a hydrogen atom)

(Scheme 2-5: wherein R is⁶Is a hydrogen atom
Excluding compounds that are[Wherein TBDMSCl is tert-butyldimethylsiloxane
Represents ril chloride, Z ¹Represents an oxygen or sulfur atom
Represent. ]

(Scheme 2-6: except for compounds in which R ⁶ is a hydrogen atom) The compound represented by the formula (10), which is a production intermediate of the compound of the present invention, can be produced, for example, according to Scheme 3.

[0159]

Embedded image

As the intermediates for the production of the compounds of the present invention, commercially available halide compounds represented by the formula (8) and alcohol compounds represented by the formula (9) may be used. Org. Chem. , 56,10
37-1041 (1991); Izvest. Aka
d. Nauk S.D. S. S. R. , Otdel. Khi
m. Nauk, 1960, 447-451 [CA (Chemical Abstract) vol 54, 22344d];
Doklady Akad. Nauk S.D. S. S. R.
132, 606 to 608 (1960) [CA (Chemical Abstract) vol 54, 22331h] or the like, or according to Scheme 4.

[0161]

Embedded image [In the formula, L ¹ represents a chlorine atom or a bromine atom, L ² represents a mesyloxy group or a tosyloxy group, Ms represents a mesyl group, Ts represents a tosyl group, and M represents the same or different halogen atom. Represent. ]

Formula (1) which is an intermediate for producing the compound of the present invention.
1) and a compound represented by the formula (12) (the formula (6)
Can be produced, for example, according to Scheme 5.

(Scheme 5-1) [In the formula, R ³⁵ represents an alcohol protecting group (for example, benzoyl group, acetyl group, etc.), and Q ³ represents an oxygen atom, a sulfur atom or an NR ²⁹ group (R ²⁹ has the same meaning as described above). Represent. ]

(Scheme 5-2) (A method for producing a compound in which A is A ² and Q ¹ is an oxygen atom)

Formula (1) which is an intermediate for producing the compound of the present invention.
The compound represented by 4) can be produced, for example, according to Scheme 6.

(Scheme 6-1) [Wherein, Y ¹ represents an oxygen atom or an NH group, and R ³⁶ represents
It represents a residue of a protecting group for a hydroxyl group of phenol or an amino group of aniline (for example, a benzoyl group, an acetyl group, a TBDMS group, etc.), and the TBDMS group represents a tert-butyldimethylsilyl group. ]

(Scheme 6-2) (Method for producing a compound wherein Y and Z are both oxygen atoms and Q ¹ is an oxygen atom (A is A ¹ )) Wherein R ³⁷ represents a methyl group or an ethyl group;
³⁸ represents a residue of a protecting group for a hydroxyl group of phenol (for example, benzoyl group, acetyl group, etc.). ]

(Scheme 6-3) (A is A^TwoAnd Q¹, Y and Z are all acids
An elemental atom and R ⁷Is a methyl group
Manufacturing method)

(Scheme 6-4) (Method for producing a compound wherein A is A ¹ , Y and Z are both oxygen atoms, and R ⁷ is a hydrogen atom) Wherein, R ³⁷ represents a methyl group or an ethyl group, R ³⁹ is a protecting group of a phenolic hydroxyl group (e.g., a benzyl group)
Represents DIBAL stands for diisobutylaluminum hydride. ]

(Scheme 6-5) (Method for producing compound wherein A is A ¹ and Y and Z are both oxygen atoms) [R ³⁹ represents a protecting group for a hydroxyl group of phenol (for example, benzyl group, etc.), R ⁴⁰ represents an acetyl group or a benzoyl group, and PCC represents pyridinium chlorochromate. ]

Formula (1) which is an intermediate for producing the compound of the present invention.
As the compound represented by 3), a commercially available compound can be used, or it can be produced, for example, according to Scheme 7.

(Method for producing compound wherein R ⁶ is not hydrogen atom) [In the formula, L ³ represents a leaving group (for example, a halogen atom, a hydroxysulfonyloxy group, a 2,4,6-trimethylbenzenesulfonyloxy group). ]

Formula (1) which is an intermediate for producing the compound of the present invention.
7) The compound represented by the formula (18), the formula (19), the formula (20) and the formula (21) may be a commercially available compound, or a method according to the literature exemplified below,
It can be produced according to other known methods. [Compound in which J is a sulfur atom in formula (33)]
Org. Chem. , 30, 1284 (1965); [Compound in which J is an oxygen atom or a sulfur atom in formula (35)] Am. Chem. Soc. , 81, 71
4 (1959); Justus Liebigs An
n. Chem. , 590, 123 (1954).

Examples of the harmful insects and harmful mites to which the compound of the present invention shows control effects include the following. Hemiptera pests: brown planthopper (Laodelfax)
striatellus), brown planthopper (Nila)
parvata lugens)
hoppers such as Gatella furcifera, and leafhoppers (Nephotettix ci)
ncticeps), Leafhopper (Em)
leafhoppers such as poasca onukii, aphids such as cotton aphids (Aphis gossypiii) and peach peach aphids (Myzus persicae), stink bugs, and whiteflies (Tr)
ialeurodes vapororiorum),
Bemisia tabaci,
Silver leaf whitefly (Bemisia arge)
whiteflies such as C. ntifoli), scale insects, hornworms, psyllids, etc. Lepidopteran pests: Chilosuppres
salis), Kobumemeiga (Cnaphalocro)
cis medicinalis), European corn borer (Ostrinia nubilalis), Shibattoga (Parapediasia terre)
llla), and Japanese scabies (Spodo)
ptera litura), Acacia litura (S)
podoptera exigua), armyworm (P
genus (Heliotis spp.), Heliospia sp., Heliospia spp., Heliospia spp., Helicoptera spp., and Helicobacter spp. Noctuids, cabbage butterfly (Pieris rapae crucivo)
ra) and white butterflies, such as Adoxopherosoraana fasciat
a), Nashihimeshinkui (Grapholitamol)
esta), codling moss (Cydia pomon)
ella) and tortoises such as peach sink moth (Car
Posina niponensis, etc., and the peach stalk moth, Lyonetia clark
ella, etc .;
horny moth moths (Phyllocnis), such as L. horny ringerniella
Scutellaria such as tis citrella, Suga such as Plutella xylostella, and pink ball worm (Pectinopho)
diptera pests such as house mosquitoes, mosquitoes, anopheles, midges, houseflies, blowflies, smelt flies, flies, flies, and flies. Crustaceans, Drosophila, Drosophila, Flyes, Blackflies, Dermatophagoides, etc. Coleoptera: Chrysomelids, Scarabaeidae, Weevil, Beetles, Ladybirds, Cerambycidae, Beetles, etc. Thrips: Thrips palmiformes Thri
thrips, such as ps palmi, Frankliniella occid
entalis, Frankliniella spp., Thrips thrips dors
alis) and other thrips such as the genus Siltthrips, and thrips, etc. Insects Pests: Insecta pests: Human fleas, etc. Lice pests: Aphids, etc. Termite pests: Termites, etc. Acarid pests: Tetranychus
spp. ), Panonychus s
pp. ), Spider mites, dust mites,
Acarid mites, ticks, etc. Furthermore, they are also effective against existing insecticides and pests that have developed resistance to acaricides.

When the compound of the present invention is used as an active ingredient of an insecticide or acaricide, it may be used as it is without adding any other components. However, usually, a solid carrier, a liquid carrier, a gaseous carrier, Mix with feed, etc., and add surfactants and other formulation auxiliaries as necessary, and add oils, emulsions, wettable powders, flowables, granules, powders, aerosols, aerosols (such as fogging), poison baits It is used after being formulated in the above. These preparations usually contain the present compound as an active ingredient in an amount of 0.01% to 95% by weight.

Examples of the solid carrier used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (sericite). , Quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, salt ammonium, etc.)
Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), and aromatic hydrocarbons (hexane, cyclohexane, kerosene, etc.). Gas oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylformamide, N,
N-dimethylacetamide, etc.), halogenated hydrocarbons
(Dichloromethane, trichloroethane, carbon tetrachloride, etc.),
Vegetable oils such as dimethyl sulfoxide, soybean oil, cottonseed oil and the like can be mentioned. Examples of the gaseous carrier, that is, propellant, include flon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas and the like. Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives and the like. can give. Pharmaceutical adjuvants such as fixatives and dispersants include, for example, casein, gelatin, polysaccharides (starch, gum arabic,
Cellulose derivatives, alginic acid, etc.), lignin derivatives,
Bentonite, saccharides, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.) can be mentioned, and as a stabilizer, for example, PAP (isopropyl isopropyl phosphate), BHT (2,6-di-tert-
Butyl-4-methylphenol), BHA (2-tert
A mixture of -butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil,
Mineral oils, surfactants, fatty acids or esters thereof and the like can be mentioned. Examples of bait baits include bait ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; and pepper powder. Attractable flavors such as food inhibitors, cheese flavors, onion flavors and the like.

The preparation thus obtained is used as it is or after dilution with water or the like. Also other pesticides,
It can be mixed with or used in combination with nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like. Such insecticides, nematicides,
As acaricides, for example, fenitrothion [O, O-
Dimethyl O- (3-methyl-4-nitrophenyl) phosphorothioate], phenthione [O, O-dimethyl O- (3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinon [O, O-diethyl-O- 2-isopropyl-6-methylpyrimidine-4-
Yl phosphorothioate], chlorpyrifos [O, O-
Diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate], acephate [O, S-dimethylacetylphosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-oxo-
1,3,4-thiadiazol-3-ylmethyl O, O
-Dimethyl phosphorodithioate], disulfotone [O, O-diethyl S-2-ethylthioethyl phosphorothioate], DDVP [2,2-dichlorovinyl dimethyl phosphate], sulphophos [O-ethyl O
-4- (methylthio) phenyl S-propyl phosphorodithioate], cyanophos [O-4-cyanophenyl O, O-dimethyl phosphorothioate], dioxabenzophos [2-methoxy-4H-1,3,2-benzo] Dioxaphosphinin-2-sulfide], dimethoate [O, O-dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphate], fentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl)]
Acetate], malathion [diethyl (dimethoxyphosphinothioylthio) succinate], trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate], azinphosmethyl [S-3,4]
-Dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O, O-dimethylphosphorodithioate], monocrotophos [dimethyl (E) -1-methyl-2- (methylcarbamoyl) vinyl phosphate ], Ethion [O, O, O ', O'-tetraethyl
S, S'-methylenebis (phosphorodithioate)],
Organic phosphorus compounds such as propenophos [O-4-bromo-2-chlorophenyl O-ethyl S-propyl phosphorothioate], BPMC (2-sec-butylphenylmethyl carbamate), benfracarb [ethyl N- [2,3-dihydro- 2,2-dimethylbenzofuran-7-yloxycarbonyl (methyl) aminothio] -N-isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-
2,2-dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], mesomil [S-methyl-N-[(methylcarbamoyl) Oxy] thioacetimidate], ethiophenecarb [2
-(Ethylthiomethyl) phenylmethylcarbamate], aldicarb [2-methyl-2- (methylthio)
Propionaldehyde O-methylcarbamoyloxy], oxamyl [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide], phenothiocarb [S-4-phenoxybutyl]
-N, N-dimethylthiocarbamate], thiodicarb [3,7,9,13-tetramethyl-5,11-dioxa-2,8,14-trithia-4,7,9,12-tetra-azapentadeca-3] , 12-diene-6,10-dione, alanicarb [ethyl (Z) -N-benzyl-N
Carbamate-based compounds such as-{[methyl (1-methylthioethylideneaminooxycarbonyl) amino] thio} -β-alaninate;
(4-ethoxyphenyl) -2-methylpropyl-3-
Phenoxybenzyl ether], fenvalerate [(RS) -α-cyano-3-phenoxybenzyl (R
S) -2- (4-chlorophenyl) -3-methylbutyrate], esfenvalerate [(S) -α-cyano-
3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-methylbutyrate], fenpropatrin [(RS) -α-cyano-3-phenoxybenzyl 2,
2,3,3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS) -α-cyano-3-
Phenoxybenzyl (1RS, 3RS) -3- (2,2
-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-methylcyclopropanecarboxylate], Cyhalothrin [(RS) -α-cyano-3-phenoxybenzyl (Z)-(1RS) -cis-3- (2
-Chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S) -α-cyano-3-phenoxybenzyl (1R, 3R)- 3 (2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate], cycloprothrine [(RS) -α-cyano-
3-phenoxybenzyl (RS) -2,2-dichloro-
1- (4-ethoxyphenyl) cyclopropanecarboxylate], fluvalinate (α-cyano-3-phenoxybenzyl N- (2-chloro-α, α, α-trifluoro-p-tolyl) -D-valinate) , Bifensulin (2-methylbiphenyl-3-ylmethyl) (Z)
-(1RS) -cis-3- (2-chloro-3,3,3
-Trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate, acrinasulin ([1R- {1α (S ^* ), 3α (Z)}]-2,2-
Dimethyl-3- [3-oxo-3- (2,2,2-trifluoro-1- (trifluoromethyl) ethoxy-1-
Propenyl) cyclopropanecarboxylic acid, (S)-
(Α) -cyano (3-phenoxyphenyl) methyl ester, 2-methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) ether, tralomethrin [(1R, 3S) 3 [(1′R
S) (1 ′, 1 ′, 2 ′, 2′-tetrabromoethyl)]-2,2-dimethylcyclopropanecarboxylic acid (S) -α-cyano-3-phenoxybenzyl ester, silafluofen [4-ethoxyphenyl] [3-
(4-fluoro-3-phenoxyphenyl) propyl]
Pyrethroid compounds such as dimethylsilane, buprofezin (2-tert-butylimino-3-isopropyl-
Thiadiazine derivatives such as 5-phenyl-1,3,5-thiadiadinan-4-one), imidacloprid [1-
Nitroimidazolidine derivatives such as (6-chloro-3-pyridylmethyl) -N-nitroimidazolidin-2-indeneamine], cartap [S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate)], thiocyclam [N , N-dimethyl-1,2,3-trithian-5-ylamine], bensultap [S, S'-2]
-Dimethylaminotrimethylene di (benzenethiosulfonate)] and the like, and acetamiprid [N-cyano-N'-methyl-N '-(6-chloro-3-pyridylmethyl) acetamidine] and the like. N-cyanoamidine derivative, endosulfan [6,7,8,
9,10,10-hexachloro-1,5,5a, 6
9,9a-Hexahydro-6,9-methano-2,4,3
-Benzodioxathiepine oxide], γ-BHC
(1,2,3,4,5,6-hexachlorocyclohexane), 1,1-bis (chlorophenyl) -2,2,2-
Chlorinated hydrocarbon compounds such as trichloroethanol, chlorfluazuron [1- (3,5-dichloro-4- (3-
Chloro-5-trifluoromethylpyridin-2-yloxy) phenyl) -3- (2,6-difluorobenzoyl) urea], teflubenzuron [1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6-
Difluorobenzoyl) urea], flufenoxuron [1- (4- (2-chloro-4-trifluoromethylphenoxy) -2-fluorophenyl) -3- (2,6-
Benzoylphenyl urea-based compounds such as difluorobenzoyl) urea, amitraz [N, N '[(methylimino) dimethylidinyl] di-2,4-xylysine], and chlordimeform [N'-(4-chloro-2-methylphenyl)- Formamidine derivatives such as N, N-dimethylmethinimidamide, diafenthiuron [N- (2,6-diisopropyl-4-phenoxyphenyl) -N′-te
thiourea derivatives such as rt-butylcarbodiimide], bromopropylate [isopropyl 4,4'-dibromobenzylate], tetradiphone [4-chlorophenyl 2,4,5-trichlorophenylsulfone], quinomethionate [S, S-6] Methylquinoxaline-2,3-
Diyldithiocarbonate], propargate [2-
(4-tert-butylphenoxy) cyclohexyl
Propyl-2-yl sulfite], fenbutatin
Oxide [bis [tris (2-methyl-2-phenylpropyl) tin] oxide], hexthiazox [(4
RS, 5RS) -5- (4-chlorophenyl) -N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], clofenthedine [3,6-bis (2-chlorophenyl) ) -1,2,4,
5-tetrazine, pyridathioben [2-tert-butyl-5- (4-tert-butylbenzylthio) -4-
Chloropyridazin-3 (2H) -one], fenpyroximate [tert-butyl (E) -4-[(1,3-
Dimethyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl] benzoate], tebufenpyrad [N-4-tert-butylbenzyl] -4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide], poly Nactin complex [tetranactin, dinactin, trinactin], milbemectin,
Avermectin, ivermectin, azadirachtin [A
ZAD], pyrimidifen [5-chloro-N- [2-
{4- (2-ethoxyethyl) -2,3-dimethylphenoxy} ethyl] -6-ethylpyrimidin-4-amine, chlorfenapyl [4-bromo-2- (4-chlorophenyl) -1-ethoxymethyl-5- Trifluoromethylpyrrole-3-carbonitrile], tebufenidide [N-tertbutyl-N '-(4-ethylbenzoyl) -3,5-dimethylbenzohydrazide], phenylpyrazole derivatives and the like.

When the compound of the present invention is used as an insecticide or acaricide for agricultural use, the application rate is usually 0.1 g to 100 g per 10 ares, and the emulsion, wettable powder, flowable and the like are diluted with water. When used as such, the application concentration is usually 1 ppm to 10000 ppm, and granules, dusts and the like are applied as they are without dilution. When used as an insecticide or acaricide for epidemics, emulsions, wettable powders, flowables, etc. are usually 0.1 pp in water.
It is applied after being diluted to m to 500 ppm, and the oil, aerosol, aerosol, poison bait and the like are applied as they are. These application rates and application concentrations vary depending on the type of preparation, application time, application place, application method, type of pest, degree of damage, and the like, and can be increased or decreased without being affected by the above range.

[0176]

EXAMPLES The present invention will be described in more detail with reference to Production Examples, Preparation Examples, Test Examples, etc., but the present invention is not limited to these Examples. First, Production Examples of the compound of the present invention will be shown.

Production of Compound (2) of the Present Invention by Production Example 1 (Production Method E) 4- (2,6-Dichloro-4- (3,3-dichloro-2)
O- (3,3-dichloro-2-propenyl) hydroxylamine hydrochloride (0.20 g) was added to a mixture of -propenyloxy) phenoxy) butyloxyacetaldehyde (0.37 g) and pyridine (10 ml), and the mixture was stirred at room temperature for 24 hours. The reaction solution was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy). ) Phenoxy) butyloxyacetaldehyde O-
(3,3-dichloro-2-propenyl) oxime 0.3
9 g were obtained. Yield 74% n _D ^24.0 1.5489 Production of Compound (12) of the Present Invention by Production Example 2 (Production Method F) 4- (2,6-Diethyl-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetaldehyde oxime 0.27 g, potassium carbonate 0.1
0 g, benzyl bromide 0.16 g and N, N-dimethylformamide 10 ml were put in a reaction vessel, and the mixture was stirred at room temperature for 24 hours. Then, the reaction solution was poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, concentrated, and the residue was subjected to silica gel chromatography to give 4- (2,6-
Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde.O
-0.21 g of benzyl oxime was obtained. 56% yield
n _D ^22.5 1.5402 Production of compound (16) of the present invention by Production Example 3 (Production Method E) 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal 0.3
O-tert was added to a mixture of 7 g and 10 ml of pyridine.
0.13 g of butylhydroxylamine hydrochloride,
After stirring at room temperature for 24 hours, the reaction solution was poured into dilute hydrochloric acid,
Extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, concentrated, and the residue was subjected to silica gel chromatography to give a residue.
(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O-te
0.22 g of rt-butyl oxime was obtained. Yield 50%
n _D ^25.2 1.5275

Production of Compound (30) of the Present Invention by Production Example 4 (Production Method E) 0.34 g of (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone and 10 ml of pyridine 0.11 g of O-ethylhydroxylamine hydrochloride was added to the mixture, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give (2,6-dichloro-4).
0.32 g of-(3,3-dichloro-2-propenyloxy) phenoxy) acetone / O-ethyloxime was obtained. Yield 81% mp 65.4 ° C Production of compound (14) of the present invention by Production Example 5 (Production Method E) 5- (2,6-dichloro-4- (3,3-dichloro-2)
O-tert-butylhydroxylamine hydrochloride (0.13 g) was added to a mixture of -propenyloxy) phenoxy) pentyloxyacetaldehyde (0.42 g) and pyridine (10 ml). After stirring at room temperature for 24 hours, the reaction solution was poured into diluted hydrochloric acid. , And extracted twice with diethyl ether.
The combined ethyl ether layers were washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3).
0.45 g of -dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O-tert-butyloxime was obtained. Yield 92% n _D ^25.2
5185 Production of Compound (17) of the Present Invention by Production Example 6 (Production Method E) 5- (2,6-Dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal 0.3
O- (3,3) was added to a mixture of 7 g and 10 ml of pyridine.
After adding 0.20 g of -dichloro-2-propenyl) hydroxylamine hydrochloride and stirring at room temperature for 24 hours, the reaction solution was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4-
0.23 g of (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (3,3-dichloro-2-propenyl) oxime was obtained. Yield 48% n
_D ^25.2 1.5559

Production of Compound (74) of the Present Invention by Production Example 7 (Production Method C) 0.58 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol (JP-A-8-33)
No. 7549), potassium carbonate 0.30 g, chloroacetaldehyde / O- (3,
0.43 g of 3-dichloro-2-propenyl) oxime and 10 ml of N, N-dimethylformamide were put in a reaction vessel, and the mixture was stirred at room temperature for 24 hours. The reaction solution was poured into water and extracted twice with diethyl ether. . The diethyl ether layers were combined, washed with water, and dried over anhydrous magnesium sulfate.
Concentrate and subject the residue to silica gel chromatography,
(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde.O-
(3,3-dichloro-2-propenyl) oxime 0.7
4 g were obtained. Yield 82% n _D ^22.3 1.5680 Preparation of compound (147) of the present invention according to Preparation Example 8 (Preparation Method E) 4- (2,6-diethyl-4- (3,3-dichloro-2)
0.15 g of hydroxylamine hydrochloride was added to a mixture of 0.75 g of -propenyloxy) phenoxy) butyloxyacetaldehyde and 10 ml of pyridine, and the mixture was stirred at room temperature for 24 hours. Extracted times. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated.
The residue was subjected to silica gel chromatography to give 4-
0.67 g of (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde oxime was obtained. Yield 75% n
_D ^24.5 1.5278 Production of Compound (152) of the Present Invention by Production Example 9 (Production Method E) 5- (2,6-Dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal 5.5
1.25 g of hydroxylamine hydrochloride was added to a mixture of 8 g and 50 ml of pyridine, and the mixture was stirred at room temperature for 24 hours.
Extracted times. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-
2.44 g of 4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal oxime were obtained. Yield 41% n _D ^23.4 1.5600

Production of Compound (234) of the Present Invention by Production Example 10 (Production Method E) 5- (2,6-Dichloro-4- (3,3-dichloro-2)
8.60 g of hydroxylamine hydrochloride was added to a mixture of 1.67 g of -propenyloxy) phenoxy) pentyloxyacetone and 30 ml of pyridine, and the mixture was stirred at room temperature for 1 hour. Extracted times. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated.
8.81 g of (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone oxime was obtained. Yield 99% n _D ^25.0
1.5460 Compound of the present invention (104) according to Production Example 11 (Production Method E)
Production of 5- (2,6-dichloro-4- (3,3-dichloro-2)
To a mixture of 0.43 g of propenyloxy) phenoxy) pentyloxyacetone and 10 ml of pyridine,
-Tert-butylhydroxylamine hydrochloride 0.15
After stirring for 24 hours at room temperature, the reaction mixture was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy). ) Phenoxy) pentyloxyacetone / O-tert-butyloxime 0.45 g
I got Yield 90% n _D ^25.5 1.5170 Compound of the present invention (177) according to Production Example 12 (Production Method G)
Production of 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone oxime 0.45 g, triethylamine 0.12
g and 10 ml of tetrahydrofuran were placed in a reaction vessel, and 0.12 g of acetic anhydride was slowly added dropwise at room temperature with stirring. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes, and then the reaction solution was poured into diluted hydrochloric acid and extracted twice with diethyl ether. Combine the diethyl ether layers and wash it sequentially with saturated aqueous sodium bicarbonate and water,
After drying over anhydrous magnesium sulfate and concentration, the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O 0.21 g of acetyl oxime was obtained. Yield 43% n _D ^25.6
1.5318

Preparation of compound (179) of the present invention according to Preparation Example 13 (Preparation Method G) 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone oxime 0.45 g, triethylamine 0.12
g and 10 ml of tetrahydrofuran were placed in a reaction vessel, and 0.25 g of 4-trifluoromethylbenzoyl chloride was slowly added dropwise at room temperature with stirring.
After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes, and then the reaction solution was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, concentrated, and the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3-dichloro-2). 0.59 g of -propenyloxy) phenoxy) pentyloxyacetone.O- (4-trifluoromethylbenzoyl) oxime was obtained.
Yield 96% n _D ^25.6 1.5300 Compound of the present invention (180) according to Production Example 14 (Production Method G)
Production of 5- (2,6-dichloro-4- (3,3-dichloro-2)
0.45 g of propenyloxy) phenoxy) pentyloxyacetone oxime and tetrahydrofuran 1
0 ml into a reaction vessel and stirring at room temperature while stirring.
0.12 g of rt-butyl isocyanate was slowly added dropwise. After the completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes, and then poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, concentrated, and the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3-dichloro-2). -Propenyloxy)
Phenoxy) pentyloxyacetone O- (N-te
0.47 g of rt-butylcarbamoyl) oxime was obtained. Yield 86% n _D ^25.6 1.5191 Compound of the present invention (216) according to Production Example 15 (Production Method G)
Production of 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone oxime 0.45 g, triethylamine 0.12
g and 10 ml of tetrahydrofuran are placed in a reaction vessel, and a solution of 0.23 g of p-toluenesulfonyl chloride in 5 ml of tetrahydrofuran is slowly added dropwise with stirring under ice-cooling. After completion of the dropwise addition, the mixture is further stirred at room temperature for 30 minutes, then the reaction mixture is poured into dilute hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to give 5- (2,6-
Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (p
-Toluenesulfonyl) oxime is obtained.

Production of Compound (217) of the Present Invention by Production Example 16 (Production Method G) 5- (2,6-Dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone oxime 0.45 g, triethylamine 0.12
g and 10 ml of tetrahydrofuran are placed in a reaction vessel, and 0.16 g of N, N-diethylcarbamoyl chloride is slowly added dropwise with stirring under ice cooling. After completion of the dropwise addition, the mixture is further stirred at room temperature for 30 minutes, then the reaction mixture is poured into dilute hydrochloric acid, and extracted twice with diethyl ether.
The diethyl ether layers are combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to give 5
-(2,6-dichloro-4- (3,3-dichloro-2-
Propenyloxy) phenoxy) pentyloxyacetone.O- (N, N-diethylcarbamoyl) oxime is obtained. Compound (218) of the present invention according to Production Example 17 (Production Method H)
Production of 5- (2,6-dichloro-4- (3,3-dichloro-2)
0.45 g of propenyloxy) phenoxy) pentyloxyacetone oxime and tetrahydrofuran 1
0 ml into a reaction vessel and stirring at room temperature while stirring.
0.14 g of rt-butyl isothiocyanate is slowly added dropwise. After completion of the dropwise addition, the mixture is further stirred at a temperature ranging from room temperature to 65 ° C., and then the reaction solution is poured into water and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (N-ter
(t-butylthiocarbamoyl) oxime is obtained. Compound (213) of the present invention according to Production Example 18 (Production Method F)
Production of 5- (2,6-dichloro-4- (3,3-dichloro-2)
0.45 g of -propenyloxy) phenoxy) pentyloxyacetone oxime and 10 ml of tert-butyl methyl ether are placed in a reaction vessel, and stirred at room temperature under a nitrogen stream at room temperature while stirring at 60% sodium hydride (oil-based).
Add 48 mg slowly. After stirring at room temperature until the generation of hydrogen is completed, chloroacetonitrile 0.11 g
At room temperature, and further stirred under reflux. After completion of the reaction, the reaction solution is poured into diluted hydrochloric acid and extracted twice with diethyl ether. Combine the diethyl ether layers, wash it with water,
After drying over anhydrous magnesium sulfate and concentration, a crude product is obtained. This crude product is subjected to silica gel chromatography to obtain 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-cyanomethyloxime.

Production of Compound (214) of the Present Invention by Production Example 19 (Production Method F) 5- (2,6-Dichloro-4- (3,3-dichloro-2)
0.45 g of -propenyloxy) phenoxy) pentyloxyacetone oxime and 10 ml of tert-butyl methyl ether are placed in a reaction vessel, and stirred at room temperature under a nitrogen stream at room temperature while stirring at 60% sodium hydride (oil-based).
Add 48 mg slowly. After stirring at room temperature until the generation of hydrogen was completed, tert-butyl bromoacetate was added.
29 g was added at room temperature, and the mixture was further stirred under reflux with heating. After completion of the reaction, the reaction solution is poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (tert-butoxycarbonylmethyl) oxime is obtained. Compound (211) of the present invention according to Production Example 20 (Production Method A)
Production of 5- (2,6-dichloro-4-hydroxyphenoxy)
0.39 g of pentyloxyacetone / O-tert-butyloxime, 0.12 g of 1,1,3-tribromo-1-propene, 0.17 g of potassium carbonate and 10 ml of N, N-dimethylformamide were placed in a reaction vessel, and the mixture was added at room temperature. After stirring for 24 hours, the reaction is poured into dilute hydrochloric acid. The mixture was extracted twice with diethyl ether, the diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated.
A crude product is obtained. This crude product was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,
3-Dibromo-2-propenyloxy) phenoxy) pentyloxyacetone O-tert-butyloxime is obtained. Compound (207) of the present invention according to Production Example 21 (Production Method C)
Preparation of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol 0.46 g, potassium carbonate 0.25 g, 1- (5- (methanesulfonyloxy) pentyloxy) -2-butanone -0.58 g of O-tert-butyl oxime and 15 ml of N, N-dimethylformamide were placed in a reaction vessel, and the mixture was stirred at 55 ° C to 60 ° C for 2 hours. Added. This was extracted twice with ethyl acetate, the ethyl acetate layers were combined, washed sequentially with dilute hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 1- (5- (2 , 6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) -2-butanone O-te
0.69 g of rt-butyl oxime was obtained. 84% yield
n _D ^23.4 1.5140

Preparation of Compound (210) of the Present Invention by Preparation Example 22 (Preparation Method D) 2- (5-hydroxypentyloxy) cyclohexanone.O-tert-butyloxime 0.45 g, 2,6
A mixture of 0.43 g of -dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, 0.39 g of triphenylphosphine and 15 ml of tetrahydrofuran was added with stirring under a nitrogen stream under ice-cooling while stirring diisopropylazodiamine. 0.30 g of carboxylate is slowly added dropwise. After stirring at room temperature for 24 hours, the reaction solution was concentrated,
Get the residue. The residue was subjected to silica gel chromatography to give 2- (5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) cyclohexanone.O-tert-butyloxime is obtained. Compound (103) of the present invention according to Production Example 23 (Production Method C)
Production of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol 0.55 g, potassium carbonate 0.29 g, 4- (methanesulfonyloxy) butyloxyacetone / O-tert-butyloxime 0.59
g and N, N-dimethylformamide (10 ml) were placed in a reaction vessel, and the mixture was stirred at 60 ° C. for 6 hours. This was extracted twice with ethyl acetate, the ethyl acetate layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 4- (2,6-dichloro-4- ( 3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone / O-tert
0.71 g of -butyl oxime was obtained. Yield 77% n
_D ^25.0 1.5170 Compound of the present invention (203) according to Production Example 24 (Production Method D)
Production of 2- (2-hydroxyethoxy) ethoxyacetone.O
A mixture of 0.51 g of tert-butyl oxime, 0.58 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, 0.58 g of triphenylphosphine and 20 ml of tetrahydrofuran was added under a nitrogen stream. Then, 0.49 g of diisopropylazodicarboxylate was slowly added dropwise while stirring under ice cooling. After stirring at room temperature for 4 hours, the reaction solution was concentrated, and the residue was subjected to silica gel chromatography to give 2- (2-
0.68 g of (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxy) ethoxyacetone / O-tert-butyloxime was obtained. Yield 68% n _D ^23.0 1.5172

Production of Compound (104) of the Present Invention by Production Example 25 (Production Method I) 5- (2,6-Dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone / oxime (0.45 g), concentrated sulfuric acid (0.3 ml) and toluene (10 ml) are placed in a reaction vessel, and while stirring under ice-cooling, isobutene gas is blown into the reaction vessel, and the mixture is further stirred at room temperature. After completion of the reaction, the reaction solution is slowly poured into a saturated aqueous solution of sodium hydrogen carbonate, and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product. This crude product is subjected to silica gel chromatography to obtain 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-tert-butyloxime. Compound (185) of the present invention according to Production Example 26 (Production Method E)
Preparation of O- (2,4,6-trimethylbenzenesulfonyl) hydroxylamine [Synthesis, 1-17 (1
977)]. To a mixture of 1.29 g and 10 ml of diethyl ether was added sodium 1,1,1,3,3,3-hexafluoro-2-propyl while stirring under ice-cooling. Add 1.14 g of oxide and add 2
Stirred for hours. The suspended reaction solution was filtered through celite, and O-
A filtrate was obtained as a diethyl ether solution of (1,1,1,3,3,3-hexafluoro-2-propyl) hydroxylamine. Diethyl ether was added to the filtrate to make the weight of the diethyl ether solution 30 g.
g of concentrated hydrochloric acid and 0.1 ml of concentrated hydrochloric acid were poured into a reaction vessel containing 0.37 g of 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal. After stirring at room temperature for 2 hours, the reaction solution was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to preparative thin-layer chromatography to give 5- (2,6-dichloro-4- (3,3-dichloro-2). -Propenyloxy) phenoxy) pentanal
O- (1,1,1,3,3,3-hexafluoro-2-
0.27 g of propyl) oxime was obtained. Yield 50%
n _D ^24.5 1.4850 Compound of the present invention (186) according to Production Example 27 (Production Method E)
Preparation of (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone 0.34 g, O
A mixture of 0.24 g of-(3- (5-trifluoromethyl-2-pyridyloxy) propyl) hydroxylamine, 0.14 g of pyridinium chloride and 10 ml of pyridine was stirred at room temperature for 2 hours, and the reaction solution was poured into diluted hydrochloric acid. And extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, and dried over anhydrous magnesium sulfate.
Concentrate and subject the residue to silica gel chromatography,
(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone.O- (3-
0.40 g of (5-trifluoromethyl-2-pyridyloxy) propyl) oxime was obtained. Yield 71% n _D
^23.0 1.5310

Next, some of the specific examples of the compounds of the present invention are shown together with the compound numbers and some of the physical properties. (1) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde / O-ethyloxime n _D ^24.0 1.5310 (2) 4- (2 6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime n _D ^24.0 1.5489 (3) 4- ( 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O- (3,3-dibromo-2-propenyl) oxime n _D ^24.5 1.5661 (4) 4 -(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde.O- (2-propenyl ) Oxime
n _D ^23.5 1.5326 (5) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde / O-benzyloxime n _D ^23.5 1.5471 (6 ) 4- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde / O-tert-butyloxime
n _D ^23.5 1.5229 (7) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O-methyl oxime n _D ^23.5 1.5374 (8 ) (Z) -4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O- (3,3-dichloro-
2-propenyl) oxime n _D ^24.6 1.5498 (9) (E) -4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O- (3,3-dichloro-
2-propenyl) oxime n _D ^24.6 1.5490 (10) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O- (3,3- Dichloro-2-propenyl) oxime n _D ^24.5 1.5213 (11) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde / O-tert-butyl Oxime
n _D ^24.5 1.4974 (12) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde / O-benzyl oxime n _D ^22.5 1.5402 (13 ) 4- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O- (4- (trifluoromethyl) benzyl) oxime n _D ^22.5 1.5166 ( 14) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O-tert-butyloxime n _D ^25.2 1.5185 (15) 5- (2 , 6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O (3,3-dichloro-2
Propenyl) oxime n _D ^25.2 1.5450 (16) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal O-tert-butyl oxime n _D ^25.2 5275 (17) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (3,3-dichloro-2-propenyl) oxime n _D ^25.2 5559 (18) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal • On-propyloxime n _D ^19.5 1.5373 (19) 5- (2 , 6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (2-propenyl) oxime n _D ^19.5 1.546 8 (20) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (3,3-dibromo-2-propenyl) oxime n _D ^23.7 5742 (21) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal · O-benzyloxime n _D ^23.7 1.5605 (22) 5- (2,6 -Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal O- (4-methoxybenzyl) oxime n _D ^21.5 1.5587 (23) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (2,4-dinitrophenyl) oxime mp.
65.2 ° C (24) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal · O- (3,3-dichloro-2-propenyl) oxime n _D ^22.6 1.5602 (25) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal.O- (3,3-dibromo-2-propenyl) oxime n _D ^22.6 1.5797 (26) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal.O-tert-butyloxime n _D ^22.6 1.5309 (27) 4 - (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal · O-benzyl-oxime ^{_{n D 22.6 1.5700 (28) 4-}} (2,6 Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal · O-ethyl oxime ^{_{n D 24.6 1.5427 (29) 4-}} (2,6- dichloro-4- (3,3-dichloro -2-propenyloxy) phenoxy) butanal · O-methyloxime n _D ^22.6 1.5496 (30) (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone · O-
Ethyl oxime mp. 65.4 ° C (31) (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone / O-
(3,3-dichloro-2-propenyl) oxime n _D ^23.2 1.5658 (32) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde.O -(3,3-Dichloro-2-propenyl) oxime (33) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde O- (3 3-dichloro-2-
Propenyl) oxime n _D ^25.6 1.5513 (34) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde O- (3,3-dichloro- 2-
Propenyl) oxime n _D ^26.0 1.5390 (35) 2- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde.O- (3,3-dichloro-2) -Propenyl) oxime (36) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde O- (3,3-dichloro-2-
Propenyl) oxime (37) 5- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde O- (3,3-dichloro-2-
Propenyl) oxime (38) 6- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde O- (3,3-dichloro-2-
Propenyl) oxime (39) 2- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde.O- (3,3-dichloro-2-
Propenyl) oxime (40) 3- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime (41) 4- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O- (3,3-dichloro-
2-propenyl) oxime (42) 5- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime (43) 6- (2-ethyl-6-methyl-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime (44) 2- (2,6-dichloro-4- (3,3-dichloro-2) -Propenyloxy) phenoxy) ethoxyacetone / O- (3,3-dichloro-2-propenyl) oxime (45) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy ) Propyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime (46) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone O- (3,3-dichloro-2-propenyl) oxime (47) 5- (2,6-dichloro-4- (3,3-dichloro-2-) Propenyloxy) phenoxy) pentyloxyacetone / O- (3,3-dichloro-2-propenyl) oxime n _D ^25.5 1.5408 (48) 6- (2,6-dichloro-4- (3,3-dichloro-) 2-propenyloxy) phenoxy) hexyloxyacetone O- (3,3-dichloro-2-propenyl) oxime (49) 2- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) ) Phenoxy) ethoxyacetone / O- (3,3-dichloro-2-propenyl) oxime (50) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy Acetone O- (3,3-dichloro-2-propenyl) oxime (51) 4- (2,6-diethyl-4- (3,3-dichloro-2-prop) Lopenyloxy) phenoxy) butyloxyacetone / O- (3,3-dichloro-2-propenyl) oxime (52) 5- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) Pentyloxyacetone O- (3,3-dichloro-2-propenyl) oxime (53) 6- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetone O- (3,3-dichloro-2-propenyl) oxime (54) 2- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethoxyacetone / O- (3,3-dichloro-2-propenyl) oxime (55) 3- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime (56) 4- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime (57) 5- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxyacetone O- (3,3-dichloro-2-propenyl) oxime (58) 6- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) hexyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime (59) 3- (2- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (60) 3- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (61) 3- (4- (2,6-dichloro-4- (3, 3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (62) 3- (5- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (63) 3- (6- (2,6-dichloro-4- (3, 3
-Dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (64) 3- (2- (2,6-diethyl-4- (3, 3
-Dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (65) 3- (3- (2,6-diethyl-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde O- (3,3-dichloro-2-propenyl) oxime (66) 3- (4- (2,6-diethyl-4- (3, 3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (67) 3- (5- (2,6-diethyl-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde O- (3,3-dichloro-2-propenyl) oxime (68) 3- (6- (2,6-diethyl-4- (3, 3
-Dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (69) 3- (2- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde.O- (3,3-
Dichloro-2-propenyl) oxime (70) 3- (3- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde.O-
(3,3-dichloro-2-propenyl) oxime (71) 3- (4- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde O- (3
3-dichloro-2-propenyl) oxime (72) 3- (5- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde.O-
(3,3-Dichloro-2-propenyl) oxime (73) 3- (6- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde.O-
(3,3-dichloro-2-propenyl) oxime (74) (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde.O- (3,3-dichloro-2 -Propenyl) oxime n _D ^22.3 1.5680 (75) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propionaldehyde O- (3,3-dichloro- 2-propenyl) oxime n _D ^23.3 1.5646 (76) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal O- (3,3-dichloro- 2-propenyl) oxime n _D ^24.5 1.5509 (77) (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetoal Dehyde-O- (3,3-dichloro-2-propenyl) oxime (78) (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone-O-
(3,3-dichloro-2-propenyl) oxime (79) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propionaldehyde.O- (3,3- Dichloro-2-propenyl) oxime (80) 4- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal.O- (3,3-dichloro-2-propenyl) Oxime (81) 5- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal O- (3,3-dichloro-2-propenyl) oxime (82) 6- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal.O- (3,3-dichloro-2-propenyl) oxime (8 ) (2-ethyl-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde · O-(3,3-dichloro-2-propenyl)
Oxime (84) (2-Ethyl-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone / O- (3,3-dichloro-2-propenyl) oxime (85) 3- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propionaldehyde.O- (3,3-dichloro-2-propenyl) oxime (86) 4- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butanal.O- (3,3-dichloro-2-propenyl) oxime (87) 5- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentanal.O- (3,3-dichloro-2-propenyl)
Oxime (88) 6- (2-Ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) hexanal.O- (3,3-dichloro-2-propenyl)
Oxime (89) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde / O-tert-butyloxime (90) 3- (2,6-dichloro- 4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde / O-tert-butyloxime n _D ^25.6 1.5253 (91) 6- (2,6-dichloro-4- (3,3 -Dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde.O-tert-butyloxime n _D ^26.0 1.5181 (92) 2- (2,6-diethyl-4- (3,3-dichloro-2-propenyl) Oxy) phenoxy) ethoxyacetaldehyde / O-tert-butyloxime (93) 3- (2,6-die 4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde / O-tert-butyloxime (94) 5- (2,6-diethyl-4- (3,3-dichloro-2) -Propenyloxy) phenoxy) pentyloxyacetaldehyde.O-tert-butyloxime (95) 6- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde.O- tert-butyl oxime (96) 2- (2-ethyl-6-methyl-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde / O-tert-butyloxime (97) 3- (2-ethyl-6-methyl-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde / O-tert-butyloxime (98) 4- (2-ethyl-6-methyl-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde / O-tert-butyloxime (99) 5- (2-ethyl-6-methyl-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde / O-tert-butyloxime

(100) 6- (2-Ethyl-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde O-te
rt-butyl oxime (101) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetone / O-tert-butyloxime (102) 3- (2,6 -Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetone / O-tert-butyloxime (103) 4- (2,6-dichloro-4- (3,3-dichloro-) 2-propenyloxy) phenoxy) butyloxyacetone / O-tert-butyloxime n _D ^25.0 1.5170 (104) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy ) pentyloxy acetone · O-tert-butyl-oxime ^{_{n D 25.5 1.5170 (105) 6-}} (2,6- dichloro - -(3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetone / O-tert-butyloxime (106) 2- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) ) Phenoxy) ethoxyacetone / O-tert-butyloxime (107) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetone / O-tert-butyloxime (108) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone / O-tert-butyloxime (109) 5- (2,6-diethyl- 4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-tert- Tyloxime (110) 6- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetone / O-tert-butyloxime (111) 2- (2-ethyl-6) -Methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxyacetone / O-tert-butyloxime (112) 3- (2-ethyl-6-methyl-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) propyloxyacetone / O-tert-butyloxime (113) 4- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone / O-tert-butyloxime (114) 5- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-tert-butyloxime (115) 6- (2-ethyl-6-methyl-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) hexyloxyacetone / O-tert-butyloxime (116) 3- (2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde / O-tert-butyloxime (117) 3- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde O-tert-
Butyl oxime (118) 3- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde O-tert-butyloxime (119) 3- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde O-tert-
Butyl oxime (120) 3- (6- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde O-tert-
Butyl oxime (121) 3- (2- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde.O-tert-butyloxime (122) 3- (3- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde O-tert-
Butyl oxime (123) 3- (4- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde / O-tert-butyloxime (124) 3- (5- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde O-tert-
Butyl oxime (125) 3- (6- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde O-tert-
Butyl oxime (126) 3- (2- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde O-tert-
Butyl oxime (127) 3- (3- (2-ethyl-6-methyl-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde O-te
rt-butyl oxime (128) 3- (4- (2-ethyl-6-methyl-4-
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde O-ter
t-Butyl oxime (129) 3- (5- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde O-te
rt-butyl oxime (130) 3- (6- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde O-te
rt-butyl oxime (131) (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde / O-tert-butyloxime n _D ^22.3 1.5371 (132) (2 6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone.O
-Tert-butyloxime (133) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propionaldehyde.O-tert-butyloxime n _D ^23.3 1.5345 (134 ) 6- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal-O-tert-butyloxime n _D ^24.5 1.5237 (135) (2,6-diethyl- 4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde.O-tert-butyloxime (136) (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) Acetone O
-Tert-butyloxime (137) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propionaldehyde / O-tert-butyloxime (138) 4- (2 6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal.O-tert-butyloxime (139) 5- (2,6-diethyl-4- (3,3-dichloro-2) -Propenyloxy) phenoxy) pentanal-O-tert-butyloxime (140) 6- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal-O-tert-butyloxime (141) (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) acetaldehyde / O-tert-butyloxime (142) (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) acetone / O-tert-butyloxime (143) 3- (2-ethyl-6-methyl-4- (3,3)
3-dichloro-2-propenyloxy) phenoxy) propionaldehyde.O-tert-butyloxime (144) 4- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butanal.O-tert-butyloxime (145) 5- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentanal O-tert-butyloxime (146) 6- (2-ethyl-6-methyl-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) hexanal-O-tert-butyloxime (147) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde Oxime n _D ^24.5 1.5278 (148) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde oxime mp. 62.8 ° C (149) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde oxime n _D ^21.2 1.5465 (150) 2- (2 , 6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetonephenone.O- (3,3-dichloro-2-propenyl)
Oxime n _D ^23.4 1.5929 (151) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetonephenone / O-tert-butyloxime n _D ^23.4 1.5622 (152) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal oxime n _D ^23.4 1.5600 (153) 5- (2,6-dichloro-4 -(3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde / O-isopropyloxime
n _D ^24.0 1.5242 (154) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde O-sec-butyl oxime n _D ^24.0 1.5211 (155) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde / O-isobutyloxime
n _D ^25.2 1.5206 (156) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde / O-neopentyloxime
n _D ^25.2 1.5106 (157) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal O- (4-trifluoromethylbenzyl) oxime n _D ^24.8 1.5345 (158) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O-methyloxime n _D ^24.7 1.5343 (159) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O-ethyloxime n _D ^24.7 1.5291 (160) 5- (2,6-dichloro-4 -(3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O-benzyloxime n _D ^24.7 1.5550 (161) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O- (2,2,2-trichloroethyl) oxime n _D ^24.4 1.5423 (162) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde O-phenyloxime n _D ^24.4 1.5613 (163) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O-cyclohexyloxime n _D ^24.4 1.5289 (164) 5- (2,6-dichloro -4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O (2,2,2-bromoethyl) oxime ^{_{n D 25.3 1.5671 (165) 5-}} (2,6- dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy acetaldehyde O- (2,2,2-trifluoroethyl) oxime n _D ^25.3 1.5058 (166) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxy Acetaldehyde / O-isopropyl oxime
n _D ^25.3 1.5266 (167) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde.O-isopropyloxime
n _D ^25.3 1.5212 (168) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde O- (2,2,2-trichloroethyl) Oxime n _D ^25.3 1.5445 (169) 6- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde O- (2,2,2-trichloroethyl ) Oxime n _D ^25.3 1.5372 (170) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal O-isopropyl oxime n _D ^25.3 1.5337 (171 ) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (2,2 - trichloroethyl) oxime ^{_{n D 25.3 1.5520 (172) 5-}} (2,6- dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal · O-phenyl-oxime n _D ^25.3 1. 5725 (173) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-isopropyloxime n _D ^25.5 1.5208 (174) 5- (2 , 6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O- (2,2,2-trichloroethyl) oxime n _D ^25.5 1.5378 (175) 5- ( 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-benzyl Oxime ^{_{n D 25.5 1.5510 (176) 5-}} (2,6- dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy acetone · O-ethyl oxime n _D ^25.5 1.5262 ( 177) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-acetyloxime n _D ^25.6 1.5318 (178) 5- (2,6 -Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-pivaloyloxime n _D ^25.6 1.5195 (179) 5- (2,6-dichloro-4- ( 3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (4-trifluoromethylbenzoyl) oxime n _D ^25.6 1.5300 (180) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (N-tert-butylcarbamoyl) oxime n _D ^25.6 1.5191 (181) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (N-phenylcarbamoyl) oxime n _D ^25.6 1.5546 (182) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde.O- (1,1,1,3,3,3
-Hexafluoro-2-propyl) oxime n _D
^24.5 1.4829 (183) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde.O- (1,1,1,3,3,
3-hexafluoro-2-propyl) oxime n _D
^24.5 1.4821 (184) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (1,1,1,3,3,3 -Hexafluoro-2-propyl) oxime n _D ^24.5
4807 (185) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal • O- (1,1,1,3,3,3-hexafluoro-2 -Propyl) oxime n _D ^24.5 1.4850 (186) (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone.O
-(3- (5-trifluoromethyl-2-pyridyloxy) propyl) oxime n _D ^23.0 1.5310 (187) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) ) Phenoxy) butanal-O-isopropyloxime (188) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal.O-isopropyloxime (189) 4- (2 , 6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal.O- (2,2,2-trichloroethyl) oxime (190) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal.O- (2,2,2-trichloroethyl) oxime (191) 4- 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone / O-isopropyloxime (192) 4- (2,6-dichloro-4- (3,3-dichloro) -2-propenyloxy) phenoxy) butyloxyacetone.O- (2,2,2-trichloroethyl)
Oxime (193) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal • O-isobutyloxime (194) 5- (2,6-dichloro-4- ( 3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-isobutyloxime (195) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal O-sec-butyl oxime (196) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone O-sec-butyl oxime (197) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal.O- (2 2,198- (2,2-tribromoethyl) oxime (198) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (2,2,2- Tribromoethyl) oxime (199) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal O- (2,2,2-trifluoroethyl) oxime

(200) 5- (2,6-dichloro-4-
(3,3-Dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O- (2,2,2-trifluoroethyl) oxime (201) 4- (2,6-dichloro-4- (3,3 -Dichloro-2-propenyloxy) phenoxy) -2-butenyloxyacetone / O-tert-butyloxime (202) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) Phenoxy) -2-butynyloxyacetone / O-tert-butyloxime (203) 2- (2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) ethoxyacetone / O-tert-butyloxime n _D ^23.0 1.5172 (204) 2- (N- (2- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -N-methylamino) ethoxyacetone
O-tert-butyl oxime (205) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) cyclohexyloxyacetone / O-tert-butyloxime (206) 7- ( 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) heptyloxyacetone / O-tert-butyloxime (207) 1- (5- (2,6-dichloro-4- ( 3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) -2-butanone.O-tert-butyloxime n _D ^23.4 1.5140 (208) 1- (5- (2,6-dichloro-4- (3 ,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) -3,3-dimethyl-2-butanone.O
-Tert-butyloxime n _D ^23.4 1.5102 (209) 2- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) acetophenone.O-tert-butyloxime n _D ^23.4 1.5483 (210) 2- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) cyclohexanone / O-tert-butyloxime (211) 5- (2,6-dichloro-4- (3,3-dibromo-2-propenyloxy) phenoxy) Pentyloxyacetone / O-tert-butyloxime (212) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-triphenylmethyloxime (213) ) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O-cyanomethyloxime (214) 5- (2,6-dichloro-4- ( 3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (t ert-butoxycarbonylmethyl) oxime (215) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O- (2,2-diethoxyethyl) Oxime (216) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone / O- (p-toluenesulfonyl) oxime (217) 5- (2 6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (N, N-diethylcarbamoyl) oxime (218) 5- (2,6-dichloro-4- ( 3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone.O- (N-tert-butylthiocarba) Moyl) oxime (219) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde oxime (220) 3- (2,6-dichloro-4- ( 3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde oxime (221) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde Oxime (222) 2- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde oxime (223) 3- (2,6-Diethyl-4- (3 3-dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde oxime 224) 5- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde oxime (225) 6- (2,6-Diethyl-4- (3,3 -Dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde oxime (226) 2- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde oxime (227) 3- (2-ethyl-6-methyl-4- (3,3)
3-Dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde oxime (228) 4- (2-ethyl-6-methyl-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde oxime (229) 5- (2-ethyl-6-methyl-4- (3,3)
3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde oxime (230) 6- (2-ethyl-6-methyl-4- (3,3)
3-Dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde oxime (231) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetone oxime (232) ) 3- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetone oxime (233) 4- (2,6-dichloro-4- (3,3- Dichloro-2-propenyloxy) phenoxy) butyloxyacetone oxime (234) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone oxime n _D ^25.0 1.5460 (235) 6- (2,6-dichloro-4- (3,3-dichloro-2-pro Nyloxy) phenoxy) hexyloxyacetone oxime (236) 2- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetone oxime (237) 3- (2,6 -Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetone oxime (238) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) Phenoxy) butyloxyacetone oxime (239) 5- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone oxime (240) 6- (2,6- Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetone Shims (241) 2- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxyacetone oxime (242) 3- (2-ethyl-6-methyl-4- (3,3)
3-Dichloro-2-propenyloxy) phenoxy) propyloxyacetone oxime (243) 4- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone oxime (244) 5- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone oxime (245) 6- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetone oxime (246) 3- (2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde oxime (247) 3- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde oxime (248) 3- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde oxime (249) 3- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde oxime (250) 3- (6- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde oxime (251) 3- (2- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde oxime (252) 3- (3- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde oxime (253) 3- (4- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde oxime (254) 3- (5- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde oxime (255) 3- (6- (2,6-diethyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde oxime (256) 3- (2- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde oxime (257) 3- (3- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde oxime (258) 3- (4- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde oxime (259) 3- (5- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde oxime (260) 3- (6- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde oxime (261) (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde oxime (262) (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone oxime (263) 3- (2,6-dichloro-4- (3,3-dichloro-) 2- (propenyloxy) phenoxy) propionaldehyde oxime (264) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal oxime (265) 6- (2 6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal Sim (266) (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde oxime (267) (2,6-Diethyl-4- (3,3-dichloro-2-) (Propenyloxy) phenoxy) acetone oxime (268) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propionaldehyde oxime (269) 4- (2,6- Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal oxime (270) 5- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal Oxime (271) 6- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) Hexanal oxime (272) (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) acetaldehyde oxime (273) (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) acetone oxime (274) 3- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propionaldehyde oxime (275) 4- (2-ethyl-6-methyl-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butanal oxime (276) 5- (2-ethyl-6-methyl-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) pentanal oxime (277) 6- (2-ethyl-6-methyl-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) hexanal oxime (278) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetonephenone oxime

Next, a production example of the carbonyl compound represented by the formula (14) will be shown. Intermediate Production Example 1 [Production of Intermediate Compound 3] 60% sodium hydride (oil-based) was added to a mixture of 56.3 g of 1,4-butanediol and 400 ml of N, N-dimethylformamide with stirring under ice cooling. ) 11.0 g was added slowly, and the mixture was stirred at room temperature for 12 hours, and then 49.3 g of bromoacetaldehyde diethyl acetal was added dropwise.
The mixture was further stirred at 60 ° C. for 8 hours. The obtained reaction solution was poured into ice water and extracted twice with ethyl acetate. The ethyl acetate layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography. −
(2,2-diethoxyethoxy) butanol 21.6 g
I got Yield 41% 4- (2,2-diethoxyethoxy) butanol 2.3
0 g, 2,6-dichloro-4- (3,3-dichloro-2
To a mixture of 2.94 g of -propenyloxy) phenol, 2.94 g of triphenylphosphine and 30 ml of tetrahydrofuran, 2.48 g of diisopropylazodicarboxylate while stirring under ice cooling and a nitrogen stream.
Was slowly added dropwise. After stirring at room temperature for 24 hours, the reaction solution was concentrated, and the residue was subjected to silica gel chromatography to give 3,5-dichloro-1- (3,3-dichloro-2).
4.48 g of -propenyloxy) -4- (4- (2,2-diethoxyethoxy) butyloxy) benzene were obtained. Yield 73% 1.81 g of 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (4- (2,2-diethoxyethoxy) butyloxy) benzene was added to acetic acid 10
To a mixture of 1 ml of concentrated hydrochloric acid and 1 ml of concentrated hydrochloric acid was added with stirring under ice-cooling, and stirring was continued for 15 minutes. The reaction was poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, dried over anhydrous magnesium sulfate, concentrated, and concentrated to give 4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde [intermediate compound 3)] 1.5
1 g was obtained. Yield 94% ¹ H-NMR (CDCl ₃ / TMS) δ (ppm):
1.92 (4H, m), 3.65 (2H, t), 3.9
9 (2H, t), 4.09 (2H, s), 4.58 (2
H, t), 6.11 (1H, t), 6.84 (2H,
9. s), 9.75 (1H, s) Intermediate Production Example 2 Production of Intermediate Compound 8) 4- (2,2-Diethoxyethoxy) butanol
0 g, 2,6-diethyl-4-benzoyloxyphenol (produced according to the method described in JP-A-8-337549), 18.9 g, triphenylphosphine 2
To a mixture of 0.2 g and 200 ml of tetrahydrofuran, 17.0 g of diisopropylazodicarboxylate was slowly dropped while stirring under a nitrogen stream under ice cooling. After stirring at room temperature for 6 hours, the reaction solution was concentrated, and the residue was subjected to silica gel chromatography to give 3,5-diethyl-1-benzoyloxy-4- (4- (2,2-diethoxyethoxy) butyloxy). 31.4 g of benzene
I got Yield 88% n _D ^24.8 1.5129 3,5-diethyl-1-benzoyloxy-4- (4-
To a solution of 31.0 g of (2,2-diethoxyethoxy) butyloxy) benzene in 100 ml of methanol was added a solution of 5.1 g of potassium hydroxide in 25 ml of water, and the mixture was stirred at room temperature for 1 hour. Dilute hydrochloric acid was added to the reaction solution to make the solution acidic, and the mixture was concentrated. Water was poured into the obtained residue, and the mixture was extracted twice with ethyl acetate. The ethyl acetate layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 3,5-diethyl-4-
(4- (2,2-diethoxyethoxy) butyloxy)
0.60 g of phenol was obtained. Yield 94% n _D ^25.0
1.4890 19.9 g of 3,5-diethyl-4- (4- (2,2-diethoxyethoxy) butyloxy) phenol,
9.20 g of 1,3-trichloro-1-propene, 9.15 g of potassium carbonate and 200 ml of N, N-dimethylformamide were put in a reaction vessel and stirred at room temperature for 24 hours. The reaction solution was poured into water and extracted twice with diethyl ether. The ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, concentrated, and the residue was subjected to silica gel chromatography to give 3,5-diethyl-1- (3,3-dichloro-2-propenyloxy) -4-. 25.4 g of (4- (2,2-diethoxyethoxy) butyloxy) benzene
I got Yield 91% n _D ^26.0 1.4991 3,5-Diethyl-1- (3,3-dichloro-2-propenyloxy) -4- (4- (2,2-diethoxyethoxy) butyloxy) benzene 9. 27 g, acetic acid 25 m
1 ml of concentrated hydrochloric acid was added to a mixture of 1 and 5 ml of water at room temperature. After stirring at room temperature for 30 minutes, the reaction solution was poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed successively with water, aqueous sodium bicarbonate and saturated saline, dried over anhydrous magnesium sulfate, and concentrated.
7.62 g of (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde [intermediate compound 8) was obtained. yield
98% ¹ H-NMR (CDCl ₃ / TMS) δ (ppm): 1.
22 (6H, t), 1.88 (4H, m), 2.63
(4H, q), 3.63 (2H, t), 3.74 (2
H, t), 4.09 (2H, s), 4.61 (2H,
d), 6.14 (1H, t), 6.57 (2H, s),
9.75 (1H, s)

Intermediate Production Example 3 Production of Intermediate Compound 19) 65.1 g of 1,5-pentanediol, 18.6 g of propargyl chloride, sodium hydroxide (powder)
0 g, benzyltriethylammonium chloride5.
69 g and 200 ml of tetrahydrofuran were put in a reaction vessel, and the mixture was stirred for 4 hours while heating under reflux. After the obtained reaction solution was filtered through celite, the filtrate was poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, concentrated, and the residue was subjected to silica gel chromatography to give 5- (2-
12.4 g of propynyloxy) pentanol were obtained. Yield 35% n _D ^26.3 1.4533 5- (2-propynyloxy) pentanol 2.35
g, 2,6-dichloro-4- (3,3-dichloro-2-
4.32 g of propenyloxy) phenol, 4.33 g of triphenylphosphine and tetrahydrofuran 3
0 ml of the mixture was stirred under ice cooling under a nitrogen stream while stirring.
3.64 g of diisopropylazodicarboxylate was slowly added dropwise. After stirring at room temperature for 24 hours, the reaction solution was concentrated, and the residue was subjected to silica gel chromatography to give 3,5-dichloro-1- (3,3-dichloro-2-).
5.17 g of propenyloxy) -4- (5- (2-propynyloxy) pentyloxy) benzene was obtained. Yield 84% n _D ^25.5 1.5400 3,5-dichloro-1- (3,3-dichloro-2-propenyloxy) -4- (5- (2-propynyloxy)
4.12 g of pentyloxy) benzene, mercury sulfate (I
I) A mixture of 0.36 g, 1 ml of a 1% aqueous sulfuric acid solution and 50 ml of tetrahydrofuran was stirred at 60 ° C. for 1 hour. After the obtained reaction solution was filtered through celite, the filtrate was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed successively with dilute hydrochloric acid and water, dried over anhydrous magnesium sulfate, concentrated, and the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (3,3- Dichloro-2-propenyloxy) phenoxy) pentyloxyacetone [intermediate compound 1
9)] 4.05 g was obtained. Yield 94% n _D ^25.5
5350 Intermediate Production Example 4 [Production of Intermediate Compound 50]] 16.3 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, potassium carbonate 2
0.7 g, 11.8 g of ethyl 5-bromovalerate, and 200 ml of N, N-dimethylformamide were placed in a reaction vessel and stirred at room temperature for 24 hours. After filtering the reaction solution,
The filtrate was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and the residue was subjected to silica gel chromatography to give 5- (2,6-dichloro-4-
18.9 g of ethyl (3,3-dichloro-2-propenyloxy) phenoxy) valerate were obtained. Yield 80% n
_D ^24.0 1.5331 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) ethyl valerate 4.0
6 g and a mixture of 50 ml of toluene under a nitrogen stream,
While stirring at -70 ° C, 0.97 mol / l diisobutylaluminum hydride (hexane solution) 10.27 m
was added dropwise over 30 minutes, and the mixture was further stirred at -70 ° C for 1 hour, and then 50 ml of a saturated aqueous ammonium chloride solution was added. After the obtained reaction solution was returned to room temperature, 50 ml of diluted hydrochloric acid was added.
And extracted twice with toluene. The combined toluene layers were washed with water, dried over anhydrous magnesium sulfate, and concentrated.
5- (2,6-dichloro-4- (3,3-dichloro-2)
3.52 g of -propenyloxy) phenoxy) pentanal [intermediate compound 50)] was obtained. Yield 96% ¹ H-NMR (CDCl ₃ / TMS) δ (ppm): 1.
80-2.11 (4H, brs), 2.58 (2H, brs)
t), 3.99 (2H, t), 4.62 (2H, d),
6.13 (1H, t), 6.85 (2H, d), 9.8
1 (1H, s) Intermediate Production Example 5 Production of Intermediate Compound 47) 2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenol 8.64 g, potassium carbonate 4.98 g , 3.36 g of chloroacetone and N, N-
50 ml of dimethylformamide was placed in a reaction vessel and stirred at room temperature for 24 hours. After filtering the reaction solution, the filtrate was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and then concentrated to give (2,6-dichloro-4- (3,3-
10.12 g of dichloro-2-propenyloxy) phenoxy) acetone [intermediate compound 47) was obtained. yield
98% mp. 83.8 ° C

Next, some specific examples of the carbonyl compound represented by the formula (14) are shown together with the compound number and some of the physical properties. 1) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde 2) 3- (2,6-dichloro-4- (3,3-dichloro-2) -Propenyloxy) phenoxy) propyloxyacetaldehyde ¹ H-NMR (CDCl ₃ / TMS) δ (ppm):
15 (2H, t), 3.83 (2H, t), 4.08
(2H, t), 4.12 (2H, s), 4.58 (2
H, d), 6.11 (1H, t), 6.84 (2H,
s), 9.76 (1H, s) 3) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde ¹ H-NMR (CDCl ₃ / TMS ) Δ (ppm):
92 (4H, m), 3.65 (2H, t), 3.99
(2H, t), 4.09 (2H, s), 4.58 (2
H, d), 6.11 (1H, t), 6.84 (2H,
s), 9.75 (1H, s) 4) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde ¹ H-NMR (CDCl ₃ / TMS ) Δ (ppm):
59-1.77 (4H, brs), 1.86 (2H, b
rs), 3.58 (2H, t), 3.96 (2H,
t), 4.07 (2H, s), 4.58 (2H, d),
6.11 (1H, t), 6.83 (2H, s), 9.7
4 (1H, s) 5) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde ¹ H-NMR (CDCl ₃ / TMS) δ (ppm) : 1.
4-1.9 (8H, m), 3.55 (2H, t), 3.
95 (2H, t), 4.06 (2H, s), 4.58
(2H, d), 6.11 (1H, t), 6.83 (2
H, s), 9.74 (1H, s) 6) 2- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde 7) 3- (2,6 -Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde 8) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyl Oxyacetaldehyde ¹ H-NMR (CDCl ₃ / TMS) δ (ppm): 1.
22 (6H, t), 1.88 (4H, m), 2.63
(4H, q), 3.63 (2H, t), 3.74 (2
H, t), 4.09 (2H, s), 4.61 (2H,
d), 6.14 (1H, t), 6.57 (2H, s),
9.75 (1H, s) 9) 5- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde ¹ H-NMR (CDCl ₃ / TMS) δ ( ppm): 1.
22 (6H, t), 1.60-1.82 (6H, br
s), 2.63 (2H, q), 3.58 (2H, t),
3.71 (2H, t), 4.07 (2H, s), 4.6
1 (2H, d), 6.14 (1H, t), 6.57 (2
H, s), 9.74 (1H, s) 10) 6- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxyphenoxy) hexyloxyacetaldehyde 11) 2- (2-ethyl -6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxyacetaldehyde 12) 3- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxyacetaldehyde 13) 4- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxyacetaldehyde 14) 5- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) pentyloxyacetaldehyde 15) 6- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) hexyloxyacetaldehyde 16) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxyacetone 17) 3- (2,6- Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetone 18) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxy Acetone 19) 5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxyacetone n _D ^25.5 1.5350 20) 6- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetone 21) 2- (2,6-diethyl) -4- (3,3-Dichloro-2-propenyloxy) phenoxy) ethoxyacetone 22) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxyacetone 23 ) 4- (2,6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxyacetone 24) 5- (2,6-Diethyl-4- (3,3-dichloro-2) -Propenyloxy) phenoxy) pentyloxyacetone 25) 6- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexyloxyacetone 26) 2- (2-ethyl-6) Methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxyacetone 27) 3- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxyacetone 28) 4- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxyacetone 29) 5- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) pentyloxyacetone 30) 6- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) hexyloxyacetone 31) 3- (2- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde 32) 3- (3- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde 33) 3- (4- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde 34) 3- (5- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde 35) 3- (6- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde 36) 3- (2- (2,6-diethyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde 37) 3- (3- (2,6-diethyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde 38) 3- (4- (2,6-diethyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde 39) 3- (5- (2,6-diethyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde 40) 3- (6- (2,6-diethyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde 41) 3- (2- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethoxy) propionaldehyde 42) 3- (3- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) propionaldehyde 43) 3- (4- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) propionaldehyde 44) 3- (5- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propionaldehyde 45) 3- (6- (2-ethyl-6-methyl-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) hexyloxy) propionaldehyde 46) (2,6-dichloro-4- (3,3-dichloro-
2-propenyloxy) phenoxy) acetaldehyde 47) (2,6-dichloro-4- (3,3-dichloro-
2-propenyloxy) phenoxy) acetone mp.
83.8 ° C. 48) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propionaldehyde ¹ H-NMR (CDCl ₃ / TMS) δ (ppm): 2.
91 (2H, dt), 4.33 (2H, t), 4.59
(2H, d), 6.11 (1H, t), 6.85 (2
H, s), 9.97 (1H, d) 49) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal ¹ H-NMR (CDCl ₃ / TMS ) Δ (ppm):
14 (2H, tt), 2.80 (2H, t), 3.99
(2H, t), 4.58 (2H, d), 6.11 (1
H, t), 6.83 (2H, s), 9.88 (1H,
s) 50) 5- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal ¹ H-NMR (CDCl ₃ / TMS) δ (ppm): 1.
80-2.11 (4H, brs), 2.58 (2H, brs)
t), 3.99 (2H, t), 4.62 (2H, d),
6.13 (1H, t), 6.85 (2H, d), 9.8
1 (1H, s) 51) 6- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal ¹ H-NMR (CDCl ₃ / TMS) δ (ppm): 1 .
50-1.95 (6H, brs), 2.48 (2H,
t), 3.95 (2H, t), 4.58 (2H, d),
6.11 (1H, t), 6.83 (2H, s), 9.7
9 (1H, s) 52) (2,6-diethyl-4- (3,3-dichloro-
2-propenyloxy) phenoxy) acetaldehyde 53) (2,6-diethyl-4- (3,3-dichloro-)
2-propenyloxy) phenoxy) acetone 54) 3- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) propionaldehyde 55) 4- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) butanal 56) 5- (2,6-diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentanal 57) 6- (2 6-Diethyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) hexanal 58) (2-ethyl-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetaldehyde 59 ) (2-Ethyl-6-methyl-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetone 60) 3- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propionaldehyde 61) 4- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butanal 62) 5- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) pentanal 63) 6- (2-ethyl-6-methyl-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) hexanal 64) 2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) acetonephenone mp. 112.5 ° C 65) 7- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) heptyloxyacetone 66) 4- (2,6-dichloro-4- (3, 3-dichloro-2-propenyloxy) phenoxy) -2-butenyloxyacetone 67) 2- (2- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxy) ethoxyacetone 68) 2- (N- (2- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -N-methylamino) ethoxyacetone 69) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy ) Cyclohexyloxyacetone

Next, a production example of the intermediate compound represented by the general formula (7) (including the compound represented by the formula (5)) will be described. Intermediate Production Example 6 [Production of Intermediate Compound 89)] 2,6-
Dichloro-4-benzoyloxyphenol (Japanese Unexamined Patent Publication No.
Manufactured according to the method described in JP-A-337549).
56 g, potassium carbonate 0.30 g, 5- (methanesulfonyloxy) pentyloxyacetone O-tert-
0.74 g of butyl oxime and 10 ml of N, N-dimethylformamide are placed in a reaction vessel, and the mixture is stirred at room temperature for 24 hours, and then the reaction solution is poured into diluted hydrochloric acid. This is extracted twice with diethyl ether, the diethyl ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to give 5- (2,6-dichloro-4- (benzoyloxy) phenoxy) pentyloxyacetone.Ot
tert-Butyl oxime is obtained. 5- (2,6-dichloro-4- (benzoyloxy) phenoxy) pentyloxyacetone / O-tert-butyloxime 0.99
g in methanol 7.5 ml was added a solution of potassium hydroxide 0.15 g in water 1.5 ml, and the mixture was stirred at room temperature for 1 hour. Dilute hydrochloric acid was added to the reaction mixture to make it acidic, and then concentrated. Water was added to the obtained residue, and the mixture was extracted twice with ethyl acetate. Combine the ethyl acetate layers,
After washing with water, drying over anhydrous magnesium sulfate and concentration, a crude product is obtained. This crude product was subjected to silica gel chromatography to give 5- (2,6-dichloro-4-hydroxyphenoxy) pentyloxyacetone / O-tert-.
Butyl oxime [intermediate compound 89)] is obtained.

Next, some specific examples of the intermediate compound represented by the formula (7) (including the compound represented by the formula (5)) are shown together with the compound numbers. 70) 4- (2,6-Dichloro-4-hydroxyphenoxy) butanal / O-isopropyloxime 71) 5- (2,6-Dichloro-4-hydroxyphenoxy) pentanal / O-isopropyloxime 72) 6- (2 , 6-Dichloro-4-hydroxyphenoxy) hexanal / O-isopropyloxime 73) 4- (2,6-dichloro-4-hydroxyphenoxy) butanal / O-tert-butyloxime 74) 5- (2,6-dichloro) -4-hydroxyphenoxy) pentanal-O-tert-butyloxime 75) 6- (2,6-dichloro-4-hydroxyphenoxy) hexanal-O-tert-butyloxime 76) 4- (2,6-dichloro-4 -Hydroxyphenoxy) butanal.O- (2,2,2-tri Loloethyl) oxime 77) 5- (2,6-dichloro-4-hydroxyphenoxy) pentanal.O- (2,2,2-trichloroethyl) oxime 78) 6- (2,6-dichloro-4-hydroxyphenoxy) Hexanal O- (2,2,2-trichloroethyl) oxime 79) 4- (2,6-dichloro-4-hydroxyphenoxy) butanal O- (3,3-dichloro-2-propenyl) oxime 80) 5 -(2,6-dichloro-4-hydroxyphenoxy) pentanal.O- (3,3-dichloro-2-propenyl) oxime 81) 6- (2,6-dichloro-4-hydroxyphenoxy) hexanal.O- ( 3,3-dichloro-2-propenyl) oxime 82) 4- (2,6-dichloro-4-hydroxyphenoxy) butyi Oxyacetaldehyde O-isopropyloxime 83) 5- (2,6-dichloro-4-hydroxyphenoxy) pentyloxyacetaldehyde O-isopropyloxime 84) 4- (2,6-dichloro-4-hydroxyphenoxy) butyloxyacetone O-isopropyl oxime 85) 5- (2,6-dichloro-4-hydroxyphenoxy) pentyloxyacetone O-isopropyl oxime 86) 4- (2,6-dichloro-4-hydroxyphenoxy) butyloxyacetaldehyde O -Tert-
Butyl oxime 87) 5- (2,6-dichloro-4-hydroxyphenoxy) pentyloxyacetaldehyde / O-tert
-Butyl oxime 88) 4- (2,6-dichloro-4-hydroxyphenoxy) butyloxyacetone / O-tert-butyloxime 89) 5- (2,6-dichloro-4-hydroxyphenoxy) pentyloxyacetone / O -Tert-butyloxime 90) 4- (2,6-dichloro-4-hydroxyphenoxy) butyloxyacetaldehyde O- (2,2
2-trichloroethyl) oxime 91) 5- (2,6-dichloro-4-hydroxyphenoxy) pentyloxyacetaldehyde O- (2
2,2-trichloroethyl) oxime 92) 4- (2,6-dichloro-4-hydroxyphenoxy) butyloxyacetone / O- (2,2,2-trichloroethyl) oxime 93) 5- (2,6- Dichloro-4-hydroxyphenoxy) pentyloxyacetone / O- (2,2,2-trichloroethyl) oxime 94) 4- (2,6-dichloro-4-hydroxyphenoxy) butyloxyacetaldehyde / O- (3,3 −
Dichloro-2-propenyl) oxime 95) 5- (2,6-dichloro-4-hydroxyphenoxy) pentyloxyacetaldehyde O- (3,3
-Dichloro-2-propenyl) oxime 96) 4- (2,6-dichloro-4-hydroxyphenoxy) butyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime 97) 5- (2,6 -Dichloro-4-hydroxyphenoxy) pentyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime

Next, a production example of the intermediate compound represented by the formula (13) will be shown. Intermediate Production Example 7 [Production of O- (3,3-dichloro-2-propenyl) hydroxylamine hydrochloride] N-hydroxyphthalimide 44 g, potassium carbonate 39
g and 400 ml of N, N-dimethylformamide were added with 41 g of 1,1,3-trichloro-1-propene at room temperature, and the mixture was stirred at room temperature for 12 hours. Was collected by filtration, washed successively with water and hexane, and dried under reduced pressure to give N- (3,3).
-Dichloro-2-propenyloxy) phthalimide 66
g was obtained. Yield 90% A mixture of 13 g of hydrazine hydrate and 17 ml of isopropyl alcohol was slowly added dropwise to a mixture of 66 g of N- (3,3-dichloro-2-propenyloxy) phthalimide and 300 ml of chloroform at room temperature. After stirring for an hour, the temperature was returned to room temperature and hexane 10
0 ml was poured. The reaction solution was filtered, and 100 ml of hexane was again added to the residue obtained by concentrating the filtrate, and the hexane solution was filtered again. Hydrogen chloride gas was blown into the filtrate, and the precipitated crystals were collected by filtration, dried under reduced pressure, and dried.
26 g of (3,3-dichloro-2-propenyl) hydroxylamine hydrochloride were obtained. Yield 60% ¹ H-NMR (CDCl ₃ -CD ₃ OD / TMS) δ (p
pm): 4.76 (2H, s), 6.17 (1H, t) Intermediate Production Example 8 [Production of O- (3- (5-trifluoromethyl-2-pyridyloxy) propyl) hydroxylamine] 2- (3-hydroxypropyloxy) -5-trifluoromethylpyridine (produced according to the method described in JP-A-9-151172) 20.0 g, N-hydroxyphthalimide 14.7 g, triphenylphosphine 2
To a mixture of 3.6 g and 200 ml of tetrahydrofuran, 20.0 g of diisopropylazodicarboxylate was slowly added dropwise while stirring under ice cooling and a nitrogen stream. After stirring at room temperature for 24 hours, the reaction solution was concentrated and the residue was subjected to silica gel chromatography to give N- (3-
27.8 g of (5-trifluoromethyl-2-pyridyloxy) propyloxy) phthalimide were obtained. Yield 8
4% mp. 97.6 ° C. In a mixture of 12.8 g of N- (3- (5-trifluoromethyl-2-pyridyloxy) propyloxy) phthalimide and 150 ml of chloroform, 1.74 g of hydrazine hydrate and 1.5 m of isopropyl alcohol at room temperature.
Then, the mixture was stirred for 3 hours while heating under reflux, then returned to room temperature and 150 ml of hexane was added. The reaction solution was filtered through celite, and 100 ml of hexane was added to the residue obtained by concentrating the filtrate, and the mixture was allowed to stand in a refrigerator for 3 days. The precipitated crystals were collected by filtration, dried under reduced pressure, and treated with O- (3-
7.0 g of (5-trifluoromethyl-2-pyridyloxy) propyl) hydroxylamine were obtained. Yield 85
% N _D ^24.0 1.4652 Intermediate Production Example 9 [Production of O- (2,2,2-trichloroethyl) hydroxylamine hydrochloride] 2.99 g of 2,2,2-trichloroethanol, O-
(2,4,6-trimethylbenzenesulfonyl) hydroxylamine [Synthesis, 1-17 (197
Production according to the method described in 7)] To a mixture of 2.15 g and 20 ml of diethyl ether, 0.68 g of sodium ethoxide was slowly added with stirring under ice-cooling. After stirring at room temperature for 5 hours, the deposited precipitate was removed by filtration through Celite, and hexane was added to the filtrate. Hydrogen chloride gas was blown into the hexane solution at room temperature, and the precipitated crystals were collected by filtration and dried under reduced pressure to obtain 1.18 g of O- (2,2,2-trichloroethyl) hydroxylamine hydrochloride. Yield 59% ¹ H-NMR (CDCl ₃ -CD ₃ OD / T
MS) [delta] (ppm): 4.84 (2H, s)

Next, a production example of the intermediate compound represented by the formula (12) (including the compound represented by the formula (6), wherein L ⁴ is a hydroxyl group) will be described. Intermediate Production Example 10 [Production of Intermediate Compound 103] 5.21 g of 1,5-pentanediol was placed in a reaction vessel, and the mixture was stirred at room temperature under a nitrogen stream at room temperature for 60% sodium hydride (oil-based). Slowly add 22 g. After stirring at room temperature until the generation of hydrogen is completed, chloroacetaldehyde / O-tert-butyl oxime 0.75
g at room temperature and slowly warm to 50 ° C. 50
After stirring for a further 3 hours at C, the reaction is poured into water and extracted twice with diethyl ether. The diethyl ether layers are combined, washed sequentially with water, dilute hydrochloric acid, and water, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to give 5
-Hydroxypentyloxyacetaldehyde / Ot
tert-Butyl oxime [intermediate compound 103)] is obtained. Intermediate Production Example 11 [Production of Intermediate Compound 105]] 13.02 g of 1,5-pentanediol, 2.40 g of sodium hydroxide (powder), 1.14 g of benzyltriethylammonium chloride, and tetrahydrofuran 1
Into a reaction vessel, while stirring, was slowly added dropwise 8.18 g of chloroacetone / O-tert-butyl oxime while stirring under reflux, and the mixture was further stirred for 8 hours. After filtering the reaction solution through celite, dilute hydrochloric acid was poured into the obtained filtrate, and the mixture was extracted twice with ethyl acetate. The ethyl acetate layers were combined, washed with diluted hydrochloric acid and water sequentially, and dried over anhydrous magnesium sulfate. Then, the residue was subjected to silica gel chromatography to obtain 6.79 g of 5-hydroxypentyloxyacetone / O-tert-butyloxime (intermediate compound 105). Yield 59% n _D
^20.0 1.4493

Next, some specific examples of the intermediate compound represented by the formula (12) (including the compound represented by the formula (6), wherein L ⁴ is a hydroxyl group) include a compound number and a certain number. Those are shown together with physical property values. 98) 4-Hydroxybutyloxyacetaldehyde
O-isopropyloxime 99) 5-hydroxypentyloxyacetaldehyde / O-isopropyloxime 100) 4-hydroxybutyloxyacetone / O-isopropyloxime 101) 5-hydroxypentyloxyacetone / O-
Isopropyl oxime 102) 4-Hydroxybutyloxyacetaldehyde / O-tert-butyloxime 103) 5-Hydroxypentyloxyacetaldehyde / O-tert-butyloxime 104) 4-Hydroxybutyloxyacetone / Ot
tert-butyl oxime n _D ^21.5 1.4477 105) 5-hydroxypentyloxyacetone O-
tert-butyl oxime n _D ^20.0 1.4493 106) 4-hydroxybutyloxyacetaldehyde O- (2,2,2-trichloroethyl) oxime 107) 5-hydroxypentyloxyacetaldehyde O- (2,2,2- Trichloroethyl) oxime 108) 4-hydroxybutyloxyacetone / O-
(2,2,2-trichloroethyl) oxime 109) 5-Hydroxypentyloxyacetone O-
(2,2,2-trichloroethyl) oxime 110) 4-hydroxybutyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime 111) 5-hydroxypentyloxyacetaldehyde.O- (3,3- Dichloro-2-propenyl) oxime 112) 4-hydroxybutyloxyacetone.O-
(3,3-Dichloro-2-propenyl) oxime 113) 5-Hydroxypentyloxyacetone O-
(3,3-dichloro-2-propenyl) oxime 114) 4-hydroxy-2-butenyloxyacetone / O-tert-butyloxime 115) 4-hydroxy-2-butynyloxyacetone / O-tert-butyloxime 116) 2- (2-Hydroxyethoxy) ethoxyacetone / O-tert-butyloxime n _D ^24.7 1.
4451 117) 2- (N- (2-hydroxyethyl) -N-methylamino) ethoxyacetone / O-tert-butyloxime 118) 4-Hydroxycyclohexyloxyacetone / O-tert-butyloxime 119) 1- (5 -Hydroxypentyloxy) -2-
Butanone / O-tert-butyl oxime n _D ^23.4
1.4479 120) 1- (5-hydroxypentyloxy) -3,
3-dimethyl-2-butanone / O-tert-butyl oxime n _D ^23.4 1.4451 121) 2- (5-hydroxypentyloxy) acetophenone / O-tert-butyl oxime n _D ^23.4
1.4490 122) 2- (5-Hydroxypentyloxy) cyclohexanone / O-tert-butyloxime

Next, an intermediate compound represented by the formula (11) (of the compounds represented by the formula (6), L ⁴ represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group or a p-toluene Including the compound which is a sulfonyloxy group). The intermediate compound produced in Intermediate Production Example 13 is also used as a raw material in Intermediate Production Example 10, and the intermediate compound produced in Intermediate Production Example 14 is the same as the intermediate production example. Also used as a raw material in 11. Intermediate Production Example 12 [Production of Intermediate Compound 129] 2.94 g of chloroacetaldehyde (40% aqueous solution)
While stirring at room temperature with O- (3,3-dichloro-
2.94 g of 2-propenyl) hydroxylamine hydrochloride
After stirring for additional 2 hours, the mixture was extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, concentrated, and chloroacetaldehyde / O- (3,3-dichloro-2-propenyl).
1.94 g of oxime (intermediate compound 120) was obtained.
Yield 96% n _D ^23.2 1.5038 Intermediate Production Example 13 [Production of Intermediate Compound 125]] 9.81 g of chloroacetaldehyde (40% aqueous solution)
To the mixture was added 3.77 g of O-tert-butylhydroxylamine hydrochloride while stirring at room temperature, and the mixture was stirred at room temperature for 2 hours and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, and chloroacetaldehyde / O-ter
t-butyl oxime [intermediate compound 125) 4.21
g was obtained. Yield 94% n _D ^23.2 1.4418 Preparation of Intermediate Product 14 [Preparation of Intermediate Compound 126] O-tert-butylhydroxylamine hydrochloride was stirred in a reaction vessel containing 9.25 g of chloroacetone at room temperature. A solution of 13.8 g of salt in 30 ml of water was added to 30
It was added dropwise over a period of minutes. After further stirring at room temperature for 2 hours,
The reaction solution was extracted with diethyl ether, and the diethyl ether layer was sequentially washed with dilute hydrochloric acid and water, and dried over anhydrous magnesium sulfate. Diethyl ether was distilled off, and chloroacetone / O-tert-butyl oxime [intermediate compound 1
26)] 16.3 g were obtained. Yield 100% n _D ^20.0
1.4366 Intermediate Production Example 15 [Production of Intermediate Compound 144)] 5-Hydroxypentyloxyacetaldehyde.O-
0.22 g of tert-butyl oxime, 0.12 g of triethylamine and 10 ml of tetrahydrofuran are put in a reaction vessel, and 0.14 g of methanesulfonyl chloride is slowly added dropwise with stirring under ice-cooling. After completion of the dropwise addition, the mixture was stirred at room temperature for an additional hour, and
Pour into 0% aqueous citric acid and extract with ethyl acetate.
The obtained ethyl acetate layer was sequentially washed with a 10% aqueous citric acid solution and saturated saline, dried over anhydrous magnesium sulfate, concentrated, and concentrated to 5- (methanesulfonyloxy) pentyloxyacetaldehyde / O-tert-butyloxime. [Intermediate compound 144)] is obtained. Intermediate Production Example 16 [Production of Intermediate Compound 142)] 5-Hydroxypentyloxyacetone / O-tert
-Butyl oxime 5.78 g, triethylamine 3.5
4 g and 20 ml of tetrahydrofuran were placed in a reaction vessel, and 3.15 g of methanesulfonyl chloride was added dropwise with stirring over 30 minutes under ice cooling. After completion of the dropwise addition, the mixture was further stirred at room temperature for 1 hour.
The mixture was poured into an aqueous citric acid solution and extracted with ethyl acetate. The obtained ethyl acetate layer was washed successively with a 10% aqueous citric acid solution and saturated saline, dried over anhydrous magnesium sulfate, concentrated, and concentrated to 5- (methanesulfonyloxy) pentyloxyacetone / O-tert-butyloxime. [Intermediate compound 142) 7.41 g was obtained. 96% yield
n _D ^20.0 1.4562

Next, an intermediate compound represented by the formula (11) (of the compounds represented by the formula (6), L ⁴ represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group or a p-toluene Some of the specific examples of the compound (including the compound which is a sulfonyloxy group) are shown together with the compound numbers and some of the physical properties. The intermediate compounds 123) to 134) are also used as raw materials for producing the intermediate compounds 98) to 122) represented by the formula (12). 123) chloroacetaldehyde / O-isopropyl oxime 124) chloroacetone / O-isopropyl oxime 125) chloroacetaldehyde / O-tert-butyl oxime n _D ^23.2 1.4418 126) chloroacetone / O-tert-butyl oxime n _D ^20.0 1 .4366 127) chloroacetaldehyde O- (2,2,2-
Trichloroethyl) oxime 128) chloroacetone O- (2,2,2-trichloroethyl) oxime 129) chloroacetaldehyde O- (3,3-dichloro-2-propenyl) oxime n _D ^23.2 1.50
38 130) Chloroacetone O- (3,3-dichloro-2)
- propenyl) oxime 131) 1-bromo-2-butanone · O-tert-butyl-oxime n _D ^23.4 1.4582 132) 1-bromo-3,3-dimethyl-2-butanone · O-tert-butyl-oxime n _D ^23.4 1.44
99 133) 2-Chloroacetophenone / O-tert-butyloxime n _D ^23.4 1.5209 134) 2-Chlorocyclohexanone / O-tert-
Butyl oxime 135) 4- (Methanesulfonyloxy) butyloxyacetaldehyde / O-isopropyl oxime 136) 5- (Methanesulfonyloxy) pentyloxyacetaldehyde / O-isopropyl oxime 137) 4- (Methanesulfonyloxy) butyloxyacetone / O -Isopropyl oxime 138) 5- (Methanesulfonyloxy) pentyloxyacetone O-isopropyloxime 139) 4- (Methanesulfonyloxy) butyloxyacetaldehyde O-tert-butyloxime 140) 5- (Methanesulfonyloxy) pentyloxy Acetaldehyde / O-tert-butyloxime 141) 4- (methanesulfonyloxy) butyloxyacetone / O-tert-butyloxime n _D ^22.1
1.4538 142) 5- (Methanesulfonyloxy) pentyloxyacetone O-tert-butyloxime n _D
^20.0 1.4562 143) 4- (Methanesulfonyloxy) butyloxyacetaldehyde.O- (2,2,2-trichloroethyl) oxime 144) 5- (Methanesulfonyloxy) pentyloxyacetaldehyde.O- (2,2,2) 2-trichloroethyl) oxime 145) 4- (methanesulfonyloxy) butyloxyacetone.O- (2,2,2-trichloroethyl) oxime 146) 5- (methanesulfonyloxy) pentyloxyacetone.O- (2 2,2-trichloroethyl) oxime 147) 4- (methanesulfonyloxy) butyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime 148) 5- (methanesulfonyloxy) pentyloxyacetaldehyde.O- (3,3-dichloro- - propenyl) oxime 149) 4- (methanesulfonyloxy) butyl oxy acetone · O-(3,3-dichloro-2-propenyl)
Oxime 150) 5- (Methanesulfonyloxy) pentyloxyacetone O- (3,3-dichloro-2-propenyl) oxime 151) 4- (Methanesulfonyloxy) 2-butenyloxyacetone O-tert-butyloxime 152) 4- (Methanesulfonyloxy) 2-butynyloxyacetone / O-tert-butyloxime 153) 2- (2- (Methanesulfonyloxy) ethoxy) ethoxyacetone / O-tert-butyloxime 154) 2- ( N- (2- (methanesulfonyloxy)
Ethyl) -N-methylamino) ethoxyacetone / O-
tert-butyl oxime 155) 4- (methanesulfonyloxy) cyclohexyloxyacetone / O-tert-butyloxime 156) 1- (5- (methanesulfonyloxy) pentyloxy) -2-butanone / O-tert-butyloxime n _D ^22.7 1.4538 157) 1- (5- (methanesulfonyloxy) pentyloxy) -3,3-dimethyl-2-butanone.Ot
ert-butyl oxime 158) 2- (5- (methanesulfonyloxy) pentyloxy) acetophenone / O-tert-butyloxime 159) 2- (5- (methanesulfonyloxy) pentyloxy) cyclohexanone / O-tert-butyloxime

Next, preparation examples are shown. Parts represent parts by weight, and the compound of the present invention is represented by the aforementioned compound number. Formulation Example 1 Emulsion 10 parts of each of the compounds (1) to (278) of the present invention are dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and polyoxyethylenestyryl phenyl ether 14
Parts and 6 parts of calcium dodecylbenzenesulfonate were added and mixed well with stirring to obtain 10% emulsions of each. Formulation Example 2 wettable powder 20 parts of each of the compounds of the present invention (1) to (278) were mixed with 4 parts of sodium lauryl sulfate and calcium ligninsulfonate 2
Parts, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of silicon earth were added and mixed well with stirring to obtain each 20% wettable powder. Formulation Example 3 Granules To 5 parts of each of the compounds of the present invention (1) to (278), 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 55 parts of clay are added and mixed with sufficient stirring. I do. Then, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain 5% granules of each.

Formulation Example 4 Powder One part of each of the present compounds (1) to (278) was dissolved in an appropriate amount of acetone, and 5 parts of synthetic hydrous silicon oxide fine powder and P
0.3 parts of AP and 93.7 parts of clay are added, mixed well with stirring, and the acetone is removed by evaporation to obtain 1% of each powder. Formulation Example 5 Flowable agent 20 parts of each of the compounds (1) to (278) of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and finely pulverized with a sand grinder. Then, 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate are added thereto, and 10 parts of propylene glycol are further added, followed by stirring and mixing.
% Flowable. Formulation Example 6 Oil agent 0.1 part of each of the present compounds (1) to (278) is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of deodorized kerosene to obtain 0.1% of each. Obtain an oil agent.

Formulation Example 7 Oily aerosol 0.1 part of each of the compounds (1) to (278) of the present invention, 0.2 part of tetramethrin, 0.1 part of d-phenothrin, 10 parts of trichloroethane and 59.6 parts of deodorized kerosene were used. After mixing and dissolving, filling in an aerosol container and attaching a valve portion, 30 parts of a propellant (liquefied petroleum gas) is filled under pressure through the valve portion to obtain each oily aerosol. Formulation Example 8 aqueous aerosol 0.2 part of each of the present compounds (1) to (278), 0.2 part of d-aresulin, 0.2 part of d-phenothrin, 5 parts of xylene, 3.4 parts of deodorized kerosene and an emulsifier @ Atmos 300
(Manufactured by Atlas Chemical Co., Ltd.)
An aerosol container is filled with 50 parts of pure water, and a valve part is attached. Then, 40 parts of a propellant (liquefied petroleum gas) is filled under pressure through the valve part to obtain each aqueous aerosol. Formulation Example 9 Mosquito coil incense 0.3 g of each of the compounds (1) to (278) of the present invention was added with 0.3 g of d-arlesrin and dissolved in 20 ml of acetone. The powder was mixed at a ratio of 4: 3: 3) with 99.4 g, and the mixture was mixed with water.
Then, the resulting mixture is molded and dried to obtain each mosquito coil.

Formulation Example 10 Electric Mosquito Mat 0.4 g of each of the compounds (1) to (278) of the present invention, 0.3 g of d-aresulin and 0.4 g of piperonyl butoxide
And add acetone to make a total of 10 ml. 0.5 ml of this solution is 2.5 cm × 1.5 cm,
0.3cm thick base for electric mat (solidified fibrils of a mixture of cotton sinter and pulp)
To obtain an electric mosquito collecting matting agent. Formulation Example 11 Heat Smoke Agent 100 mg of each of the compounds of the present invention (1) to (278) is dissolved in an appropriate amount of acetone, and impregnated into a 4.0 cm × 4.0 cm, 1.2 cm thick porous ceramic plate. To obtain a heated smoker. Formulation Example 12 Poison bait 10 mg of each of the compounds of the present invention (1) to (278) was dissolved in 0.5 ml of acetone, and this solution was added to animal solid feed powder.
(Creative feed powder CE-2 for breeding and breeding, product of Nippon Clea Co., Ltd.) 5 g and uniformly mixed. The acetone is then evaporated to dryness to obtain each poison bait.

Next, Test Examples show that the compounds of the present invention are useful as active ingredients for insecticides and acaricides. The compounds of the present invention are indicated by the above-mentioned compound numbers, and the compounds used as comparative controls are indicated by the following compound symbols. Compound (A): 4- (3-chloro-2-propenyloxy) phenoxyacetone / O-ethyloxime [Compound 9 described in JP-A-61-72733] Test Example 1 [Spodoptera li
Insecticidal test for Tura)] 2 ml of a 200-fold diluted solution (500 ppm) of water of a test compound preparation obtained according to Formulation Example 1 or 2 was prepared with a diameter of 1
13 g of artificial feed (Insector LF: manufactured by Nihon Nosan Co., Ltd.) prepared in a 1 cm polyethylene cup was impregnated.
Five four-instar larvae of Spodoptera litura were released therein, and after 6 days, their survival was confirmed, and the mortality was determined. As a result, the compounds of the present invention (1) to (31), (33), (34), (47),
(74) to (76), (90), (91), (10
3), (104), (131), (133), (13)
4), (147) to (150), (152) to (18)
6) and (203) each showed a mortality of 80% or more. In contrast, the mortality of the compound (A) was 0%. Test Example 2 [Plugella xyloste
Insecticidal Test Against Ila)] A spreading agent (New Rinault: manufactured by Nippon Agrochemicals Co., Ltd.) was added to a dilution of water (50 ppm) of the test compound preparation obtained according to Preparation Example 1 at a dilution equivalent to 3000 times. For cabbage cultivated in pots (fourth to fifth leaf stages), 25 per pot
ml was sprayed. After air-drying the treated plants, ten third-instar larvae of the Japanese moth were released, and the mortality was determined 4 days later.
As a result, the compounds of the present invention (1) to (22), (24) to
(29), (33), (34), (47), (75),
(76), (90), (91), (103), (10
4), (134), (153) to (161), (16)
3) to (176), (180), (182) to (18)
5) showed a mortality of 80% or more. In contrast, the mortality of the compound (A) was 0%.

Test Example 3 [Heliothis Vire
Insecticidal test against scens] 0.2 ml of a dilution of water (100 ppm) of the test compound preparation obtained according to Preparation Example 1 was dropped on the surface of a 3 g artificial feed prepared in a 30 ml polyethylene cup, and the mixture was homogenized. Spread out. After air drying, Heliothis vir
One second instar larva of Escens was released per cup. 1
Ten were tested per treatment. After 7 days, the larval mortality was determined. As a result, the compounds of the present invention (3), (5), (1)
1), (14) to (17), (25) to (27), (33),
(34), (47), (76), (90), (91),
(104), (134), (153) to (156), (16)
0), (161), (163) to (169), (171), (17)
3) to (175) each showed a mortality of 80% or more. Test Example 4 [Helicoverpa ar
Insecticidal test against Migera) Cotton leaf pieces (5 cm diameter) are immersed in a diluent (100 ppm) of water of a test compound preparation obtained according to Preparation Example 1 for 10 seconds, air-dried, and then polyethylene having a diameter of 5.5 cm. Put in cup. One of the third instar larvae of Helicoverpa armigera was placed therein per cup. Ten animals were tested per treatment. 5
Larval mortality was determined days later. As a result, the compound of the present invention
(2)-(6), (11), (14), (17), (24)-
(26), (91), and (104) are mortality rates of 80%, respectively.
The above is shown. On the other hand, the mortality of the compound (A) is 0.
%Met.

Test Example 5 [Cydring Moss (Cydia
Insecticidal Test Against Pomonella) 0.2 ml of a dilution of water (100 ppm) of the test compound preparation obtained according to Formulation Example 1 was dropped on a surface of 3 g of artificial feed prepared in a 30 ml polyethylene cup. Spread evenly. After air-drying, wax paper (approximately 2.5 cm square) on which about 20 eggs just before hatching of codling moss were laid was put. There were four per processing. After 7 days, the larval mortality was determined. As a result, the compounds of the present invention (1), (2),
(6), (10), (11), (14) to (16), (25),
(27), (33), (34), (47), (76), (9
0), (91), (153)-(156), (158)-
(176) showed a mortality of 80% or more. Test Example 6 [Tetranychus urt
acaricidal test against icae)] About 20 female spider mite female adults were released on a plastic cup planted seven days after sowing in the cruciferous bean (primary leaf stage),
After standing for 6 days, a 200-fold diluted solution (500 ppm) of water of the test compound preparation obtained according to Preparation Example 1 or 2 with water 1
5 ml was sprayed. Eight days later, the effect of each compound was determined according to the following criteria. -: Almost no damage and no surviving insects. ±: Slightly damaged. There are a few surviving insects. +: Both damage and surviving insects are slightly less than no treatment. ++: Equivalent to no processing. As a result, the compounds of the present invention (6), (104), (173),
The effect of (178) was-or ±, while the effect of compound (A) was +.

Test Example 7 [Musca domestic
Insecticidal Test for Stica)] A filter paper of the same size is spread on the bottom of a polyethylene cup having a diameter of 5.5 cm, and a 200-fold diluted solution (500 ppm) of water of the test compound preparation obtained according to Preparation Example 1 or 2 with water. 7m
1 was dropped on a filter paper, and about 30 mg of sucrose was uniformly added as a bait. Ten female female house flies were released into them, covered with a lid, and one day later, their survival was examined to determine the mortality. As a result, the compounds of the present invention (1), (4), (6), (7), (1
1) to (16), (18), (19), (22), (2)
8), (29), (153), (155), (15
8), (159), (165) to (167), (170),
(173), (175), (176), (180),
(203) each showed a mortality of 80% or more. On the other hand, the mortality of the compound (A) used as a control was 0%.
%Met.

The compound of the present invention exhibits excellent insecticidal and acaricidal activity.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/40 101 A01N 43/40 101A C07C 251/52 C07C 251/52 251/54 251/54 317/18 317/18 317 / 28 317/28 323/12 323/12 323/47 323/47 C07D 213/46 C07D 213/46 213/63 213/63

Claims (62)

[Claims] 1. Equation (1) In the formula, R ¹ , R ² and R ³ are each independently a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms,
Represents a haloalkoxy group, a nitro group or a cyano group having 1 to 3 carbon atoms, R ⁴ represents a 3,3-dihalogeno-2-propenyl group, a represents an integer of 0 to 2, Y represents an oxygen atom, sulfur Z represents an oxygen atom, a sulfur atom or an NR ⁵ group, R ⁵ represents a hydrogen atom, an acetyl group or an alkyl group having 1 to 3 carbon atoms, R ⁶ represents a hydrogen atom, 1 carbon atom To 8 alkyl groups, C2 to C6 haloalkyl groups, C3 to C6 alkenyl groups, C3 to C6 haloalkenyl groups, C3 to C6 alkynyl groups, C3 to C6 halo Represents an alkynyl group or a triphenylmethyl group, or has 1 to 4 carbon atoms
Represents a cycloalkyl group having 3 to 7 carbon atoms which may be substituted with an alkyl group, or having 4 to 10 carbon atoms which may have a ring portion substituted with an alkyl group having 1 to 4 carbon atoms. A cycloalkylalkyl) group, or a cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms in the ring portion. Represents a (cycloalkenylalkyl) group having 6 to 8 carbon atoms, which may be substituted, or a cyano group, a nitro group, an (alkoxy having 1 to 4 carbon atoms) carbonyl group, an alkylthio having 1 to 4 carbon atoms. Represents an alkyl group having 1 to 6 carbon atoms and substituted by at least one group selected from a group or an alkoxy group having 1 to 4 carbon atoms; [Wherein, (R ⁸ ) _b represents 0 to 5 identical or different halogen atoms, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, and an alkenyl group having 2 to 6 carbon atoms. A haloalkenyl group having 2 to 6 carbon atoms, 2 carbon atoms
To 6 alkynyl groups, C2 to C6 haloalkynyl groups, C1 to C6 alkoxy groups, C1 to C3
Haloalkoxy group, an alkenyloxy group having 3 to 6 carbon atoms, a haloalkenyloxy group having 3 to 6 carbon atoms, an alkynyloxy group having 3 to 6 carbon atoms, a haloalkynyloxy group having 3 to 6 carbon atoms, Represents 1 to 5 alkoxy) carbonyl, cyano or nitro;
⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a trifluoromethyl group, and D is a group represented by the formula -CH = or a nitrogen atom. J represents an oxygen atom or a sulfur atom, b represents an integer of 0 to 5, d represents an integer of 1 to 3, e
Represents an integer of 0 to 3, f represents an integer of 2 to 4,
R ¹⁵ and R ¹⁸ represent an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, or a halogen atom An alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, and 1 to 4 carbon atoms.
Represents a phenyl group which may be substituted with an alkoxy group or a haloalkoxy group having 1 to 3 carbon atoms, wherein R ¹⁶ and R ¹⁷ each independently represent an alkyl group having 1 to 6 carbon atoms, Haloalkyl group having 6 to 6 carbon atoms, alkenyl group having 3 to 6 carbon atoms, haloalkenyl group having 3 to 6 carbon atoms, alkynyl group having 3 to 6 carbon atoms, haloalkynyl group having 3 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms Represents an alkyl group or a halogen atom, having 1 to 4 carbon atoms
Represents a phenyl group which may be substituted by an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 3 carbon atoms, or a ring having a halogen atom And a benzyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a haloalkoxy group having 1 to 3 carbon atoms. Represents T ¹ , T ² , T ³ , T ⁴ , T ⁵ , T ⁶ or T ⁷ , wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms. Or 3 carbon atoms
Or a cycloalkyl group having 1 to 6 carbon atoms, or a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a haloalkoxy group having 1 to 3 carbon atoms Represents a phenyl group which may be substituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a carbon atom having 1 to 3 carbon atoms. Represents a benzyl group which may be substituted with a haloalkoxy group of 1 to 3, or represents a cyano group or (alkoxy having 1 to 4 carbon atoms) carbonyl group, or has 1 carbon atom substituted with one cyano group. Represents an alkyl group having 1 to 3 carbon atoms, or 1 to 3 carbon atoms substituted by one (alkoxy having 1 to 4 carbon atoms) carbonyl group.
A represents the formula (3): A ¹ :—( CR ¹⁹ = CR ²⁰ ) _h — (CR ²¹ R ²² ) _i —A ² :—( CR ¹⁹ = CR ²⁰ ) _h — (CR ²¹ R ²²⁾ in _j -Q ¹ -G- [wherein, R ^19, R ²⁰ and R ²¹ are each independently a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms, it represents a trifluoromethyl group, R ²² is Hydrogen atom, 1 to 3 carbon atoms
Represents an alkyl group or a trifluoromethyl group,
Or in A ^1, if h is is and i is 1 and 0, by the R ²² and R ⁷ are attached at the ends, optionally trimethylene group which may be substituted with an alkyl group having 1 to 3 carbon atoms, A tetramethylene group, a pentamethylene group may be formed, or when h is 0 and j is 1 in A ² , R ²² and R ⁷ are bonded at the terminal to form a carbon atom having 1 carbon atom. To form a trimethylene group, a tetramethylene group, or a pentamethylene group which may be substituted with an alkyl group from 1 to 3. h represents an integer of 0 or 1, i represents an integer of 1 to 6, j represents an integer of 1 to 3, Q ¹ represents an oxygen atom, a S (O) _y group or an NR ²⁹ group;
R ²⁹ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, y represents an integer of 0 to 2, and G represents a compound represented by the formula (4): G ¹ :—( CR ²³ R ²⁴ ) _k —G ² : — _{^{(CR 23 R 24) m -CR}} 25 = CR 26 - (CR 27 R 28) n - G 3 :-( CR 23 R 24) m -C≡C- (CR 25 R 26) n - G 4: - (CR ²³ R ²⁴ ) _p -E- (CR ²⁵ R ²⁶ ) _q -G ⁵ :-( CR ²³ R ²⁴ ) _r -Q ^2- (CR ²⁵ R ²⁶ ) _s- (where R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ and R ²⁸ are
Each independently represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a trifluoromethyl group, and k represents 2 to 8
M represents an integer of 1 to 3, n represents an integer of 1 to 3, p represents an integer of 0 or 1, and q represents 0.
Or represents an integer of 1; r represents an integer of 2 to 4;
Represents an integer of 2 to 4, Q ² represents an oxygen atom, an S (O) _z group or an NR ³⁰ group, R ³⁰ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and z represents 0 to 2 Represents an integer of
Represents a cycloalkylene group having 5 or 6 carbon atoms. ) Represents G ¹ , G ² , G ³ , G ⁴ or G ⁵ . A ¹ or A ² represented by the following formula: An oxime compound represented by｝. 2. The method according to claim 1, wherein both Y and Z are oxygen atoms.
The oxime compound according to the above. 3. The oxime compound according to claim 1, wherein a is 0. 4. The oxime compound according to claim ¹ , wherein R ¹ , R ² and R ³ are each independently a halogen atom or an alkyl group having 1 to 3 carbon atoms. 5. A method according to claim ¹ , wherein A is A ^1.
The oxime compound according to the above. 6. A method according to claim 1, wherein A is A ^2.
The oxime compound according to the above. 7. The oxime compound according to claim 6, wherein Q ¹ is an oxygen atom. 8. R ⁶ is an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, and 3 carbon atoms.
Or an alkynyl group having 3 to 6 carbon atoms or a haloalkynyl group having 3 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring Is a (cycloalkylalkyl) group having 4 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or 1
A cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with an alkyl group having 4 to 4 carbon atoms, or a cycloalkenyl group having 6 to 8 carbon atoms which may have a ring portion substituted with an alkyl group having 1 to 4 carbon atoms. A (cycloalkenylalkyl) group, or a cyano group, a nitro group,
Of 1 to 6 carbon atoms substituted by at least one of an alkoxy) carbonyl group, an alkylthio group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms.
The oxime-based compound according to any one of claims 1 to 7, which is an alkyl group represented by the formula: 9. The oxime compound according to claim 1, wherein R ⁶ is a hydrogen atom. 10. R ⁶ is triphenylmethyl group, T ^1, T ²
Alternatively oxime compound according to claim 1 which is T ^3. 11. The oxime compound according to claim 1, wherein R ⁶ is T ⁴ , T ⁵ , T ⁶ or T ⁷ . 12. The method according to claim 1, wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms. Oxime compounds. 13. R ⁷ is a halogen atom, an alkyl group having 1 to 4 carbon atoms is substituted with a haloalkoxy group a haloalkyl group having 1 to 3 carbon atoms, alkoxy groups or 1 carbon atoms of 1 to 3 carbon atoms 3 Or a phenyl group which may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a ring having 1 to 3 carbon atoms. The oxime compound according to any one of claims 1 to 11, which is a benzyl group optionally substituted with a haloalkoxy group. 14. A is A ¹ or A is A ² and G is G ¹ and k is an integer from 2 to 6, or A is A ² And when G is G ² , R ⁶ is an alkyl group having 1 to 8 carbon atoms;
A haloalkyl group having 2 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, or a haloalkynyl group having 3 to 6 carbon atoms, Or a cycloalkyl group having 3 to 7 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a carbon atom which may be substituted in the ring portion with an alkyl group having 1 to 4 carbon atoms. A (cycloalkylalkyl) group having 4 to 10 carbon atoms, a cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring portion having 1 carbon atom. from either a 4 alkyl group from carbon atoms 6 be replaced by 8 (cycloalkenylalkyl) group, or a T ¹ or T ^2, and, R ⁷ is a hydrogen atom, or 1 carbon atoms Claims 1 to 4 oxime compounds according alkyl group or 1 to 6 carbon atoms which is 3 haloalkyl group. 15. A is A ¹ and R ⁶ is an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms,
An alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms or a haloalkynyl group having 3 to 6 carbon atoms, or an alkyl group having 1 to 4 carbon atoms Is a cycloalkyl group having 3 to 7 carbon atoms which may be substituted with, or a cycloalkyl group having 4 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. A) a cycloalkenyl group having 5 to 6 carbon atoms, which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring portion substituted with an alkyl group having 1 to 4 carbon atoms. one of carbon atoms 6 even if it is 8 (cycloalkenylalkyl) group, or a T ¹ or T ^2, and, R ⁷ is a hydrogen atom, an alkyl group or a carbon number from 1 to 6 carbon atoms 1 Oxime compound according to claim 14, wherein a haloalkyl group et 3. 16. A is A ² and G is G ¹ ;
And k is an integer of 2 to 6, or A is A ²
And when G is G ² , R ⁶ represents an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, and 3 to 6 carbon atoms.
Or a haloalkynyl group having 3 to 6 carbon atoms or a haloalkynyl group having 3 to 6 carbon atoms, or a cycloalkyl having 3 to 7 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. (Cycloalkylalkyl) having 4 to 10 carbon atoms which may be an alkyl group or a ring part of which may be substituted by an alkyl group having 1 to 4 carbon atoms.
Or a cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring portion having been substituted with an alkyl group having 1 to 4 carbon atoms. Or a (cycloalkenylalkyl) group having 6 to 8 carbon atoms, or T ¹ or T ²
The oxime compound according to claim 14, wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms. 17. The oxime compound according to claim 16, wherein Q ¹ is an oxygen atom. 18. R ⁶ is an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, and 3 to 6 carbon atoms. Is an alkynyl group or a haloalkynyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 3 to 7 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring moiety A (cycloalkylalkyl) group having 4 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or 5 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. Or a cycloalkenyl group having 6 to 6 carbon atoms, or a (cycloalkenylalkyl) group having 6 to 8 carbon atoms, wherein the ring portion may be substituted with an alkyl group having 1 to 4 carbon atoms. 16 or 17 oxime compounds according. 19. The method according to claim 1, wherein R ⁶ is T ¹ or T ^2.
The oxime compound according to 4, 15, 16 or 17. 20. A wherein A is A ¹ and R ²¹ and R ²²
Are both hydrogen atoms, h is 0, and i
Is an integer from 3 to 5, or A is A ² ,
And G is G ¹ , R ²¹ , R ²² , R ²³ and R ²⁴ are all hydrogen atoms, h is 0, Q ¹ is an oxygen atom, and j is 1 And k is 3 to 6
R ² and R ³ are each independently a chlorine atom or an alkyl group having 1 to 3 carbon atoms, a is 0, and R ⁴ is 3,3-dichloro -2-propenyl group or 3,3-dibromo-2-
A propenyl group, and R ⁶ is an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 2 to 4 carbon atoms,
The oxime compound according to claim 2, which is an alkenyl group having 1 to 6 carbon atoms or a haloalkenyl group having 3 to 6 carbon atoms, and wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group. 21. A wherein A is A ¹ and R ²¹ and R ²²
Are both hydrogen atoms, h is 0, i is an integer of 3 to 5, and R ² and R ³ are each independently a chlorine atom or an alkyl group having 1 to 3 carbon atoms. And a is 0, and R ⁴ is a 3,3-dichloro-2-propenyl group or a 3,3-dibromo-2-propenyl group, and R ⁶ has 1 to 5 carbon atoms. An alkyl group, a haloalkyl group having 2 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms or a haloalkenyl group having 3 to 6 carbon atoms, and R ⁷ is a hydrogen atom, 1 to 4 carbon atoms.
21. The oxime compound according to claim 20, which is an alkyl group or a trifluoromethyl group. 22. A is A ² and G is G ¹ ;
And R ²¹ , R ²² , R ²³ and R ²⁴ are all hydrogen atoms, h is 0, Q ¹ is an oxygen atom, j is 1, and k is 3 to An integer of 6
And R ² and R ³ are each independently a chlorine atom or an alkyl group having 1 to 3 carbon atoms, a is 0, and R ⁴ is a 3,3-dichloro-2-propenyl group or A 3,3-dibromo-2-propenyl group, wherein R ⁶ is an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 2 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, or 3 to 6 carbon atoms; Is a haloalkenyl group, and
The oxime compound according to claim 20, wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group. 23. R ² and R ³ are both chlorine atoms, R ⁴ is a 3,3-dichloro-2-propenyl group, and R ⁶ is an isopropyl group, an isobutyl group,
c-butyl group, tert-butyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group,
2,2,2-tribromoethyl group, 1,1,1,3
3,3-hexafluoro-2-propyl group or 3,3
22. The oxime compound according to claim 21, which is a -dichloro-2-propenyl group and R ⁷ is a hydrogen atom. 24. R ² and R ³ are both chlorine atoms, R ⁴ is a 3,3-dichloro-2-propenyl group, and R ⁶ is an isopropyl group, an isobutyl group, s
ec-butyl group, tert-butyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 2,2,2-tribromoethyl group, 1,1,1,
A 3,3,3-hexafluoro-2-propyl group or a 3,3-dichloro-2-propenyl group, and R
23. The oxime compound according to claim 22, wherein ⁷ is a hydrogen atom or a methyl group. 25. One compound selected from the group consisting of the following compounds. 4- (2,6-dichloro-4- (3,3-dichloro-2
-Propenyloxy) phenoxy) butanal-O-isopropyloxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal • O-
Isopropyl oxime 6- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) hexanal-O-
Isopropyl oxime 4- (2,6-dichloro-4- (3,3-dichloro-2
-Propenyloxy) phenoxy) butanal-Ot
tert-butyl oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal • O-
tert-butyl oxime 6- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) hexanal-O-
tert-butyl oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butanal-O-
(2,2,2-trichloroethyl) oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal • O-
(2,2,2-trichloroethyl) oxime 6- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) hexanal-O-
(2,2,2-trichloroethyl) oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butanal-O-
(3,3-dichloro-2-propenyl) oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal • O-
(3,3-dichloro-2-propenyl) oxime 6- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) hexanal-O-
(3,3-dichloro-2-propenyl) oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetaldehyde / O-isopropyloxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetaldehyde.O-isopropyloxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetone / O-isopropyloxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone / O-isopropyloxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetaldehyde / O-tert-butyloxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetaldehyde / O-tert-butyloxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetone / O-tert-butyloxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone / O-tert-butyloxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetaldehyde O- (2,2,2-trichloroethyl) oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetaldehyde O- (2,2,2-trichloroethyl)
Oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetone / O- (2,2,2-trichloroethyl) oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone O- (2,2,2-trichloroethyl) oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetaldehyde.O- (3,3-dichloro-2-propenyl) oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetone.O- (3,3-dichloro-2-propenyl) oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone O- (3,3-dichloro-2-propenyl) oxime 26. A is A ¹ or A is A ² and G is G ¹ and k is an integer from 2 to 6, or A is A ² And when G is G ² , R ⁶ is a hydrogen atom, and R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms. The oxime compound according to the above. 27. A method according to claim 27, wherein R ² and R ³ are each independently a halogen atom or an alkyl group having 1 to 3 carbon atoms, a is 0, and both Y and Z are oxygen atoms. Item 27. The oxime compound according to Item 26. 28. The method according to claim 28, wherein A is A ¹ , R ⁶ is a hydrogen atom, and R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms. Item 28. The oxime compound according to Item 27. 29. Both R ²¹ and R ²² are hydrogen atoms,
29. The oxime compound according to claim 28, wherein h is 0 and R ⁷ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. 30. A is A ² and G is G ¹ ;
And, when k is an integer of 2 to 6, or when A is A ² and G is G ² , Q ¹ is an oxygen atom, R ⁶ is a hydrogen atom, And R ⁷ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms.
The oxime compound according to the above. 31. G is G ¹ and R ²¹ , R ²² , R
31. The method according to claim 30, wherein ²³ and R ²⁴ are all hydrogen atoms, h is 0, j is 1, and R ⁷ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Oxime compounds. 32. A is A ¹ and R ²¹ and R ²²
Are both hydrogen atoms, h is 0, and i
Is an integer of 3 to 5, R ² and R ³ are both chlorine atoms, R ⁴ is a 3,3-dichloro-2-propenyl group, and R ⁷ is a hydrogen atom The oxime compound according to claim 27. 33. A is A ² and R ²¹ , R ²² , R
²³ and R ²⁴ are both hydrogen atoms, h is 0, Q ¹ is an oxygen atom, j is 1, k is an integer of 4 or 5, and R is ² and R ³
Is a chlorine atom, R ⁴ is a 3,3-dichloro-2-propenyl group, and R ⁷ is a hydrogen atom or a methyl group. 34. One compound selected from the group consisting of the following compounds. 4- (2,6-dichloro-4- (3,3-dichloro-2
-Propenyloxy) phenoxy) butanal oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentanal oxime 6- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) hexanal oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetaldehyde oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetaldehyde oxime 4- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) butyloxyacetone oxime 5- (2,6-dichloro-4- (3,3-dichloro-2)
-Propenyloxy) phenoxy) pentyloxyacetone oxime 35. An insecticide or acaricide comprising the oxime compound according to any one of claims 1 to 34 as an active ingredient. 36. Equation (5) 中 wherein, R ³¹ represents R ⁶ other than a hydrogen atom, and R ¹ ,
R ² , R ³ , R ⁶ , R ⁷ , a, A and Z have the same meaning as in claim 1. A phenolic compound represented by｝. 37. The phenolic compound according to claim 36, wherein Z is an oxygen atom. 38. The phenolic compound according to claim 36, wherein a is 0. 39. The phenolic compound according to claim 36, wherein R ¹ , R ² and R ³ are each independently a halogen atom or an alkyl group having 1 to 3 carbon atoms. 40. A phenolic compound as claimed in any one of claims 36 to 39 A is A ^1. 41. The phenolic compound according to any one of claims 36 to 39, wherein A is A ² and G is G ¹ . 42. The phenolic compound according to any one of claims 36 to 39, wherein A is A ² and G is G ² . 43. The phenolic compound according to claim 36, wherein A is A ² and G is G ³ . 44. The phenolic compound according to claim 36, wherein A is A ² and G is G ⁴ . 45. The phenolic compound according to claim 36, wherein A is A ² and G is G ⁵ . 46. A is A ¹ and R ²¹ and R ²²
Are both hydrogen atoms, h is 0, and i
Is an integer of 3 to 5, or A is A ² , G is G ¹ , and R ²¹ , R ²² , R ²³ and R ²⁴ are all hydrogen atoms, and h is 0,
And when Q ¹ is an oxygen atom, j is 1, and k is an integer of 3 to 6, Z is an oxygen atom, and R ² and R ³ are each independently Is a chlorine atom or an alkyl group having 1 to 3 carbon atoms, a is 0, and R ³¹ is an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 2 to 4 carbon atoms, and 3 carbon atoms. 37. The phenolic compound according to claim 36, which is an alkenyl group having 3 to 6 carbon atoms or a haloalkenyl group having 3 to 6 carbon atoms, and wherein R ⁷ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group. . 47. A is A ¹ and R ²¹ and R ²²
Are both hydrogen atoms, h is 0, i is an integer from 3 to 5, Z is an oxygen atom, and
R ² and R ³ are each independently a chlorine atom or an alkyl group having 1 to 3 carbon atoms, a is 0, and R ³¹ is an alkyl group having 1 to 5 carbon atoms, To 4 haloalkyl group, alkenyl group having 3 to 6 carbon atoms or haloalkenyl group having 3 to 6 carbon atoms, and R ⁷ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group. 47. The phenolic compound according to claim 46. 48. A is A ² and R ²¹ , R ²² , R
²³ and R ²⁴ are both hydrogen atoms, h is 0, Q ¹ is an oxygen atom, j is 1, k is an integer of 3 to 6, and Z is Is an oxygen atom, and R ² and R ³ are each independently a chlorine atom or an alkyl group having 1 to 3 carbon atoms, and a
Is 0, and R ³¹ is an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 2 to 4 carbon atoms, and 3 to 6 carbon atoms.
47. An alkenyl group or a haloalkenyl group having 3 to 6 carbon atoms, and R ⁷ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group.
The phenolic compound according to the above. 49. Both R ² and R ³ are chlorine atoms, and R ³¹ is isopropyl, isobutyl, sec-
Butyl group, tert-butyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 2,
2,2-tribromoethyl group, 1,1,1,3,3,3
- a hexafluoro-2-propyl or 3,3-dichloro-2-propenyl group, and, R ⁷ is a phenolic compound according to claim 47, wherein a hydrogen atom. 50. Both R ² and R ³ are chlorine atoms, and R ³¹ is isopropyl, isobutyl, sec-
Butyl group, tert-butyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 2,
2,2-tribromoethyl group, 1,1,1,3,3,3
- a hexafluoro-2-propyl or 3,3-dichloro-2-propenyl group, and a phenolic compound according to claim 48, wherein R ⁷ is a hydrogen atom or a methyl group. (51) a compound selected from the group consisting of the following compounds: 4- (2,6-dichloro-4-hydroxyphenoxy)
Butanal / O-isopropyl oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentanal O-isopropyl oxime 6- (2,6-dichloro-4-hydroxyphenoxy)
Hexanal / O-isopropyl oxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butanal / O-tert-butyl oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentanal O-tert-butyl oxime 6- (2,6-dichloro-4-hydroxyphenoxy)
Hexanal / O-tert-butyloxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butanal O- (2,2,2-trichloroethyl) oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentanal O- (2,2,2-trichloroethyl)
Oxime 6- (2,6-dichloro-4-hydroxyphenoxy)
Hexanal / O- (2,2,2-trichloroethyl)
Oxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butanal O- (3,3-dichloro-2-propenyl) oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentanal O- (3,3-dichloro-2-propenyl) oxime 6- (2,6-dichloro-4-hydroxyphenoxy)
Hexanal O- (3,3-dichloro-2-propenyl) oxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetaldehyde / O-isopropyl oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetaldehyde / O-isopropyloxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetone / O-isopropyloxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetone / O-isopropyloxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetaldehyde / O-tert-butyloxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetaldehyde / O-tert-butyloxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetone / O-tert-butyloxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetone / O-tert-butyloxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetaldehyde / O- (2,2,2-trichloroethyl) oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetaldehyde O- (2,2,2-
Trichloroethyl) oxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetone / O- (2,2,2-trichloroethyl) oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetone / O- (2,2,2-trichloroethyl) oxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetaldehyde O- (3,3-dichloro-2-propenyl) oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetaldehyde O- (3,3-dichloro-2-propenyl) oxime 4- (2,6-dichloro-4-hydroxyphenoxy)
Butyloxyacetone O- (3,3-dichloro-2-
Propenyl) oxime 5- (2,6-dichloro-4-hydroxyphenoxy)
Pentyloxyacetone O- (3,3-dichloro-2
-Propenyl) oxime 52. The formula (6) R³²ON = CR⁷-CR³³R³⁴-OG⁶-L^Four 中 where R⁷Has the same meaning as in claim 1;³²Represents an alkyl group having 1 to 8 carbon atoms, and an alkyl group having 2 to 6 carbon atoms.
Haloalkyl group, alkenyl group having 3 to 6 carbon atoms, carbon
A haloalkenyl group having 3 to 6 carbon atoms,
A quinyl group, a haloalkynyl group having 3 to 6 carbon atoms or
Represents a phenylphenyl group, or has 1 to 4 carbon atoms
3 to 7 carbon atoms which may be substituted with an alkyl group
Represents a cycloalkyl group or has 1 ring carbon
Having 4 carbon atoms, which may be substituted with an alkyl group
Or 10 (cycloalkylalkyl) groups, or
Or may be substituted with an alkyl group having 1 to 4 carbon atoms.
Represents a cycloalkenyl group having 5 to 6 carbon atoms, or
Or the ring is substituted with an alkyl group having 1 to 4 carbon atoms.
C 6 to C 8 (cycloalkenylalkyl)
A) or a T in formula (2)¹, T^TwoMa
Or T^ThreeAnd R³³Is a hydrogen atom or a group having 1 to 3 carbon atoms
Represents an alkyl group of³⁴Is a hydrogen atom or 1 carbon atom
Represents three alkyl groups or R³⁴And R ⁷And end
By bonding at the end, an alkyl group having 1 to 3 carbon atoms
A trimethylene group which may be substituted with
And a pentamethylene group may be formed. L^FourIs hydroxyl
Group, chlorine atom, bromine atom, iodine atom, methanesulfoni
Oxy group or p-toluenesulfonyloxy group
Then G⁶Is the equation (22) G⁷:-( CR⁴¹R⁴²)_k-G⁸:-( CR⁴¹R⁴²)_m―CR⁴³= CR⁴⁴― (CR⁴⁵R⁴⁶)_n-G⁹:-( CR⁴¹R⁴²)_m―C≡C― (CR⁴³R⁴⁴)_n-(Where R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵And R⁴⁶Is
Each independently represents a hydrogen atom or an alkyl having 1 to 3 carbon atoms;
Represents a kill group, k represents an integer of 2 to 8, and m represents 1 to
Represents an integer of 3, and n represents an integer of 1 to 3. )
G⁷, G⁸Or G⁹Represents Compound represented by｝. 53. The compound according to claim 52, wherein L ⁴ is a hydroxyl group. 54. The compound according to claim 52, wherein L ⁴ is a chlorine atom, a bromine atom or an iodine atom. 55. The compound according to claim 52, wherein L ⁴ is a methanesulfonyloxy group or a p-toluenesulfonyloxy group. 56. ^R32 is an alkyl group having 1 to 8 carbon atoms, a haloalkyl group having 2 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a haloalkenyl group having 3 to 6 carbon atoms, and a carbon atom having 3 to 6 carbon atoms. An alkynyl group, a haloalkynyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 3 to 7 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a ring moiety A (cycloalkylalkyl) group having 4 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or 5 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. The cycloalkenyl group having from 6 to 6 or a (cycloalkenylalkyl) group having 6 to 8 carbon atoms, wherein the ring portion may be substituted with an alkyl group having 1 to 4 carbon atoms. Compounds according to any misalignment. 57. R ³² is T ^1, T ^2, T ³ or a compound according to any one of claims 52 to 55 is a triphenylmethyl group. 58. R ⁷ is a hydrogen atom, claim a cycloalkyl group of alkyl group having 1 to 6 carbon atoms, a haloalkyl group having from 1 to 3 carbon atoms, or from 3 to 6 carbon atoms 52-57
The compound according to any one of the above. 59. R ⁷ is substituted by a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a haloalkoxy group having 1 to 3 carbon atoms. Or a phenyl group which may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms,
The compound according to any one of claims 52 to 57, which is a benzyl group which may be substituted with an alkoxy group having 1 to 3 or a haloalkoxy group having 1 to 3 carbon atoms. 60. R ³² is an alkyl group having 1 to 5 carbon atoms,
A haloalkyl group having 2 to 4 carbon atoms, an alkenyl group having 3 to 6 carbon atoms or a haloalkenyl group having 3 to 6 carbon atoms, and R ⁷ is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or trifluoro A methyl group and R ³³
And R ³⁴ are both hydrogen atoms, and G ⁶ is a G ^7, and R ⁴¹ and R ⁴² are both hydrogen atoms, and, according to claim 53 k is an integer from 3 to 6, 54. The compound according to 54 or 55. (61) ^R32 is an isopropyl group, an isobutyl group,
sec-butyl group, tert-butyl group, 2,2,2-
Trifluoroethyl group, 2,2,2-trichloroethyl group, 2,2,2-tribromoethyl group, 1,1,1,
A 3,3,3-hexafluoro-2-propyl group or a 3,3-dichloro-2-propenyl group, and R
61. The compound according to claim 60, wherein ⁷ is a hydrogen atom or a methyl group. 62. One compound selected from the group consisting of the following compounds. 4-hydroxybutyloxyacetaldehyde / O-isopropyl oxime 5-hydroxypentyloxyacetaldehyde / O-
Isopropyl oxime 4-hydroxybutyloxyacetone / O-isopropyloxime 5-hydroxypentyloxyacetone / O-isopropyloxime 4-hydroxybutyloxyacetaldehyde / Ot
tert-butyl oxime 5-hydroxypentyloxyacetaldehyde / O-
tert-butyl oxime 4-hydroxybutyloxyacetone / O-tert-
Butyl oxime 5-hydroxypentyloxyacetone / O-tert
-Butyloxime 4-hydroxybutyloxyacetaldehyde / O-
(2,2,2-trichloroethyl) oxime 5-hydroxypentyloxyacetaldehyde / O-
(2,2,2-trichloroethyl) oxime 4-hydroxybutyloxyacetone.O- (2,2
2-trichloroethyl) oxime 5-hydroxypentyloxyacetone O- (2
2,2-Trichloroethyl) oxime 4-hydroxybutyloxyacetaldehyde / O-
(3,3-dichloro-2-propenyl) oxime 5-hydroxypentyloxyacetaldehyde O-
(3,3-dichloro-2-propenyl) oxime 4-hydroxybutyloxyacetone.O- (3,3-
Dichloro-2-propenyl) oxime 5-hydroxypentyloxyacetone.O- (3,3
-Dichloro-2-propenyl) oxime 4- (methanesulfonyloxy) butyloxyacetaldehyde / O-isopropyloxime 5- (methanesulfonyloxy) pentyloxyacetaldehyde / O-isopropyloxime 4- (methanesulfonyloxy) butyloxyacetone
O-isopropyloxime 5- (methanesulfonyloxy) pentyloxyacetone / O-isopropyloxime 4- (methanesulfonyloxy) butyloxyacetaldehyde / O-tert-butyloxime 5- (methanesulfonyloxy) pentyloxyacetaldehyde / O-tert -Butyl oxime 4- (methanesulfonyloxy) butyloxyacetone
O-tert-butyl oxime 5- (methanesulfonyloxy) pentyloxyacetone / O-tert-butyloxime 4- (methanesulfonyloxy) butyloxyacetaldehyde / O- (2,2,2-trichloroethyl) oxime 5- ( (Methanesulfonyloxy) pentyloxyacetaldehyde / O- (2,2,2-trichloroethyl) oxime 4- (methanesulfonyloxy) butyloxyacetone /
O- (2,2,2-trichloroethyl) oxime 5- (methanesulfonyloxy) pentyloxyacetone / O- (2,2,2-trichloroethyl) oxime 4- (methanesulfonyloxy) butyloxyacetaldehyde / O- (3,3-dichloro-2-propenyl) oxime 5- (methanesulfonyloxy) pentyloxyacetaldehyde O- (3,3-dichloro-2-propenyl)
Oxime 4- (methanesulfonyloxy) butyloxyacetone
O- (3,3-dichloro-2-propenyl) oxime 5- (methanesulfonyloxy) pentyloxyacetone / O- (3,3-dichloro-2-propenyl) oxime