JPH11152258A - Oxime-based compound, its use and intermediate for producing the same compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having excellent insecticidal and tick-killing activity. SOLUTION: Thus compound is expressed by formula I [R<1-3> are each a halogen or the like; R<4> is 3,3-dihalogeno-2-propenyl; (a) is 0-2; Y is 0 or the like; Z is 0 or the like; R<5> is a 1-3C alkyl or the like; R<6> is a 1-8C alkyl or the like; R<7> is a 1-6C alkyl; A is OCH2 or the like], e.g. 4-(2,6-dichloro-4-(3,3 dichloro-2-propenyloxy)phenoxy)methylbenzaldehyde.O-sec-butyloxime. The compound is obtained e.g. by reacting a compound of formula II with a halide compound of formula; L-R<4> (L is a halogen, mesyloxy or tosyloxy) preferably in the presence of a base in an inert solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

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

[0002]

2. Description of the Related Art It has been reported that certain oxime compounds can be used as active ingredients in insecticides.
No. 4 publication. However, these compounds are not always sufficient as active ingredients of insecticides and acaricides in terms of insecticidal efficacy and the like.

[0003]

Means for Solving the Problems In view of the above circumstances, the present inventors have conducted intensive studies to find a compound having excellent insecticidal and acaricidal activity, and as a result, have obtained an oxime represented by the following formula (1). The present inventors have found that the compound has excellent insecticidal and acaricidal activity, and have completed the present invention. That is,
The present invention relates to formula (1) In the formula, R ¹ , R ² and R ³ each independently represent a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a nitro group or a cyano group. R ⁴ represents 3,
Represents 3-dihalogeno-2-propenyl group, a represents an integer of 0 to 2, Y represents an oxygen atom, a sulfur atom or an NH group, Z is an oxygen atom, a sulfur atom or NR ⁵ group, ^{R 5} Represents a hydrogen atom, an acetyl group or a C1-C3 alkyl group, and R ⁶ represents a hydrogen atom, a C1-C8 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl. Group, a C3-C6 haloalkynyl group, a triphenylmethyl group, a C3-C7 cycloalkyl group in which the ring is optionally substituted with a C1-C4 alkyl group, and a C3-C7 cycloalkyl group in which the ring is substituted with a C1-C4 alkyl group A good C4 to C10 (cycloalkylalkyl) group, a C5 to C6 cycloalkenyl group whose ring portion may be substituted with a C1 to C4 alkyl group or a C1 to C6 (cycloalkylalkyl) group Represents a C6-C8 (cycloalkenylalkyl) group which may be substituted by a 4-alkyl group, or represents a cyano group, a nitro group, a (C1-C4 alkoxy) carbonyl group, a C1-C4 alkylthio group or a C1-C4 alkoxy group Optionally substituted with a group
Represents a -C6 alkyl group or a compound of the formula (2) (In the formula, b represents an integer of 0 to 5, and (R ¹⁰ ) _b represents 0
From 5 identical or different halogen atoms, C1 to
C6 alkyl group, C1-C3 haloalkyl group, C2-C
6 alkenyl group, C2-C6 haloalkenyl group, C2-
C6 alkynyl group, C2-C6 haloalkynyl group, C1
-C6 alkoxy group, C1-C3 haloalkoxy group, C
3-C6 alkenyloxy group, C3-C6 haloalkenyloxy group, C3-C6 alkynyloxy group, C3-C
6 haloalkynyloxy group, (C1-C5 alkoxy)
Represents a carbonyl group, a cyano group or a nitro group,
R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each independently represent a hydrogen atom, a C1-C3 alkyl group or a trifluoromethyl group, D represents a —CH ＝ group or a nitrogen atom, and J represents an oxygen atom or Represents a sulfur atom, 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 is a C1-C6 alkyl group, C1-C3
Haloalkyl group, C2-C6 alkenyl group or C3
Represents a phenyl group which may be substituted with a C1 to C6 cycloalkyl group, or a halogen atom, a C1 to C4 alkyl group, a C1 to C3 haloalkyl group, a C1 to C4 alkoxy group or a C1 to C3 haloalkoxy group;
R ¹⁶ and R ⁴² are each independently a C1-C6 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl group, a C3-C6 haloalkynyl group or C3
Represents a C6 cycloalkyl group, or a phenyl group which may be substituted with a halogen atom, a C1-C4 alkyl group, a C1-C3 haloalkyl group, a C1-C4 alkoxy group or a C1-C3 haloalkoxy group. Or a benzyl group in which the ring portion may be substituted with a halogen atom, a C1-C4 alkyl group, a C1-C3 haloalkyl group, a C1-C4 alkoxy group or a C1-C3 haloalkoxy group. ^T 1 -1, T represented by)
^{1 -2, T 1 -3, T} 1 -4, T 1 -5, represents ^T 1 -6 or ^T 1 -7, ^{R 7} is a hydrogen atom, C1 -C6 alkyl groups, C1 to C3 haloalkyl group or C3 ~ C6 cycloalkyl group or a halogen atom, C1
-C4 alkyl group, C1-C3 haloalkyl group, C1-
Represents a phenyl group which may be substituted with a C3 alkoxy group or a C1 to C3 haloalkoxy group, or
The ring is a halogen atom, a C1-C4 alkyl group, a C1-C4
3 haloalkyl group, C1-C3 alkoxy group or C
A represents a benzyl group which may be substituted with a 1 to C3 haloalkoxy group, and A represents a compound of the formula (3) A-1: -U ^1- (CR ¹⁹ R ²⁰ ) _t- (CR ²³ =
_{^{CR 24) h - (CR 25}} R 26) u - (CR 27 = C
_{^{R 28) p - (CR 29}} R 30) j - A-2: -U 2 - (CR 19 R 20) j - (CR 23 =
_{^{CR 24) h - (CR 25}} R 26) u - (CR 27 = C
_{^{R 28) p - (CR 29}} R 30) v - A-3: -U 1 - (CR 19 R 20) t - (CR 23 =
CR ²⁴ ) _h- (CR ²⁵ R ²⁶ ) _j -Q ^1- (CR
_{^{27 R 28) v - (CR}} 29 = CR 30) p - (CR
_{^{31 R 32) w - A-}} 4: -U 2 - (CR 19 R 20) j - (CR 23 =
CR ²⁴ ) _h- (CR ²⁵ R ²⁶ ) _v -Q ^1- (CR
_{^{27 R 28) w - (CR}} 29 = CR 30) p - (CR
_{^{31 R 32) x - A-}} 5: -U 1 - (CR 19 R 20) t -Q 1 - (CR
_{^{23 R 24) h -E- (CR}} 25 R 26) p - A-6: -U 1 - (CR 19 R 20) t -Q 1 - (CR
_{^{23 R 24) j -C≡C- (CR}} 25 R 26) m - [ ^{wherein, R 19, R 20, R} 23, R 24, R 25, R
²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R
³² independently represents a hydrogen atom, a C1 to C3 alkyl group or a trifluoromethyl group, h represents 0 or 1, j represents an integer of 1 to 3, and m represents an integer of 1 to 3 , P represents 0 or 1, t represents an integer of 0 to 3, u represents an integer of 0 to 3, v represents an integer of 1 to 4, w represents an integer of 1 to 4, x represents Represents an integer of 1 to 4, Q ¹ represents an oxygen atom, an S (O) _y group or an NR ³³ group, R ³³ represents a hydrogen atom or a C 1 to C 3 alkyl group, and y is an integer of 0 to 2. And E represents a C5-C6 cycloalkylene group. U ¹ is the formula ⁽⁴⁾ -G 1 -W- (wherein, W is represents a heterocyclic ring which may optionally be a benzene ring or substituted also be substituted, ^{G 1} has the formula ⁽⁵⁾ G 1 -1 _{^{:-( CR 35 R 36) a1 -}} G 1 -2 :-( CR 35 R 36) b1 -Q 2 - (CR
³⁷ R ³⁸ ) _d1 − (wherein Q ² represents an oxygen atom, an S (O) _z group or NR ³⁴
R ³⁴ represents a hydrogen atom or a C1-C3 alkyl group, and z represents an integer of 0-2. R ³⁵ , R ³⁶ ,
R ³⁷ and R ³⁸ each independently represent a hydrogen atom,
Represents a 1-C3 alkyl group or a trifluoromethyl group, (a1) represents an integer of 0-4, and (b1) represents 1-3
And (d1) represents an integer of 0 to 2. ) Represents a ^G 1 -1 or ^G 1 -2 represented by. Wherein U ² is a group represented by the formula (6) -G ¹ -W-G ^2- (wherein W and G ¹ have the same meanings as above, G ² is an oxygen atom, S (O) _e1 or NR ³⁹ ;
³⁹ represents a hydrogen atom or a C1-C3 alkyl group,
(E1) represents an integer of 0 to 2. ). A-1, A-2, A-3, A-4, A
Represents -5 or A-6. Provided are an oxime-based compound represented by｝ (hereinafter, referred to as the present compound) and an insecticide and acaricide containing the same as an active ingredient.

Among the compounds represented by the formula (1), oxime compounds in which R ⁶ is a hydrogen atom are useful not only as the compounds of the present invention but also as intermediates for the production thereof. The present invention further provides a compound of formula (7) useful as an intermediate for producing the compound of the present invention. In the formula, R ² , R ³ , R ⁷ , R ¹⁹ , R ²⁰ and j represent the same meaning as described above, and R ⁴¹ represents 3,3-dichloro-2-
Represents a propenyl group, a 3,3-dibromo-2-propenyl group or a 3-bromo-3-chloro-2-propenyl group. Compound represented by｝, formula (8) 中 wherein R ² , R ³ , R ⁷ , R ¹⁹ , R ²⁰ , R ²⁹ ,
R ³⁰ , R ⁴¹ , v and j represent the same meaning as described above. ｝
And a compound represented by the formula (9): Wherein R ¹ , R ² , R ³ , R ⁶ , R ⁷ , A, Z and a
Has the same meaning as described above. The present invention also provides a phenolic compound represented by｝ (excluding a compound in which R ⁶ is a hydrogen atom).

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, R ¹ , R ² , R
^The halogen atom represented by ³ , R ¹⁰ and R ⁴⁰ is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and R ¹ , R ² , R ³ , R ⁵ , R ¹¹ , R ¹² ,
R ¹³ , R ¹⁴ , R ¹⁹ , R ²⁰ , R ²³ , R ²⁴ , R
^{25, R 26, R 27,} R 28, R 29, R 30, R
³¹ , ^R32 , ^R33 , ^R34 , ^R35 , ^R36 , R
^37, C1 to C3 and the alkyl group represented by ^{R 38} and ^{R 39,} a methyl group, an ethyl group, an n- propyl group or an isopropyl group, a C1~C8 alkyl group represented by ^{R 6,} for example, , Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s
ec-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-
A 1-methylbutyl group, an n-octyl group, a 1-methylheptyl group, or the like, and R ⁷ , R ¹⁰ , R ¹⁵ , R ¹⁶ and R
^The C1-C6 alkyl group represented by ⁴² includes, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group,
-Butyl group, isobutyl group, sec-butyl group, ter
t-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 ,
A 3-methylpentyl group, a 1,3-dimethylbutyl group and the like, and a C1-C4 alkyl group represented by R ⁴⁰ means a methyl group, an ethyl group, an n-propyl group, an isopropyl group,
an n-butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, and R ¹ , R ² , R ³ , R ⁷ ,
The C1-C3 haloalkyl group represented by R ¹⁰ , R ¹⁵ and R ⁴⁰ is, for example, a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group, a 1-fluoroethyl group, a 1-chloroethyl group, a 1-bromoethyl Group, perfluoroethyl group, 2-bromo-1,1,2,2
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, 2-chloropropyl group, 2-bromopropyl group, 2-iodopropyl group,
A 2,3-dibromopropyl group or the like, and R ¹ , R ² , R
³ and a C1~C3 alkoxy group represented by ^{R 40} is,
A methoxy group, an ethoxy group, an n-propyloxy group or an isopropyloxy group, and R ¹⁰ , R ¹⁷ and R
^The C1-C6 alkoxy group represented by ¹⁸ is, for example,
Methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, neopentyloxy Tert-pentyloxy group, 1-ethylpropyloxy group, n-hexyloxy group, isohexyloxy group, 2-ethylbutyloxy group, 1-methylpentyloxy group, 1-ethylbutyloxy group, 3-methylpentyl An oxy group, a 1,3-dimethylbutyloxy group, etc., and R ¹ , R ² , R ³ , R ¹⁰
And The C1~C3 haloalkoxy group represented by ^{R 40,} for example, a trifluoromethoxy group, bromodifluoromethoxy 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-bromo- 1,1,2-trifluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2
-A trichloroethoxy group, a 2,2,2-tribromoethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2-bromoethoxy group, a 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-trifluoropropyloxy 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-dibromopropyloxy group and the like,

C2 represented by R ⁶ , R ¹⁶ and R ⁴²
-C6 haloalkyl group includes, for example, 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,
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- A bromohexyl group and the like, and a C3-C6 alkenyl group includes, for example, an allyl group, a 2-butenyl group, a 3-butenyl group,
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-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 and the like, and the C3-C6 haloalkenyl group includes, 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-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-pentenyl group, 6,6-dichloro- 5-hexenyl group, 6,6-dibromo-5-hexenyl group and the like, and the C3-C6 alkynyl group includes, for example, 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-butynyl group, 1-ethyl-3 -Butynyl group, 2-ethyl-3-butynyl group and the like, and the C3-C6 haloalkynyl group is
For example, a 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-chlorohexynyl group, 6-bromohexynyl And C2 to C6 alkenyl groups represented by R ¹⁰ and R ¹⁵ include, for example, vinyl group, 1-propenyl group, 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, and the like;

[0007] represented by ^{R 10,} the C2~C6 haloalkenyl, for example, 2-chloroethenyl group, 2-bromoethenyl group, 2,2-dichloroethene pantothenyl 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-pentenyl group, 6,6
-Dichloro-5-hexenyl group, 6,6-dibromo-5
-Hexenyl group and the like, and the C2-C6 alkynyl group includes, for example, ethynyl group, 1-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-butynyl group, 1-ethyl- 3-butynyl group, 2-ethyl-3-
And C2-C6 haloalkynyl groups include, for example, 2-chloroethynyl group, 2-bromoethynyl group, 3-chloro-2-propynyl group, and 3-bromo-2 group.
-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-hexynyl group and the like;
-C6 alkenyloxy group includes, for example, allyloxy group, 2-butenyloxy group, 3-butenyloxy group,
-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, 4-methyl-4-pentenyloxy group, and the like; The C6 haloalkenyloxy group includes, for example, a 3-chloro-2-propenyloxy group, a 3-bromo-2-propenyloxy group, a 2-chloro-2-propenyloxy group, a 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-tetra Fluoro-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, 6,6-
A dichloro-5-hexenyloxy group, a 6,6-dibromo-5-hexenyloxy group and the like, and the C3-C6 alkynyloxy group 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;
The 3-C6 haloalkynyloxy group includes, for example, a 3-chloro-2-propynyloxy group, a 3-bromo-2-propynyloxy group, a 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 group, 4-bromo-1-methyl-2-butynyloxy group, 4-bromo-1 -Methyl-3-butynyloxy group, 4-bromo-2-methyl-3-butynyloxy group, 6-chloro-5-hexynyloxy group, 6-bromo-5-hexynyloxy group and the like, and a (C1-C5 alkoxy) carbonyl group Is, for example, methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, sec-butyloxycarbonyl group, tert-butyloxycarbonyl group , N-pentyloxycarbonyl group, isopentyl Aryloxycarbonyl group, neopentyloxy group, tert- pentyloxycarbonyl group, a and a 1-ethylpropyl oxycarbonyl ^group, C3～ represented by ^{R 7,} R 15, R ¹⁶ and ^{R 42}
C6 cycloalkyl group and cyclopropyl group, cyclobutyl group, cyclopentyl group or cyclohexyl group, a 3,3-dihalogeno-substituted-2-propenyl group represented by ^{R 4,} preferably, 3,3-dichloro-propenyl Group, 3,3-dibromopropenyl group, 3-bromo-3
-Chloropropenyl group, 3-chloro-3-fluoropropenyl group, 3-bromo-3-fluoropropenyl group,

The C 3 -C 7 cycloalkyl group represented by R ⁶ , whose ring portion may be substituted by a C 1 -C 4 alkyl group, is, for example, a cyclopropyl group, a cyclobutyl group,
Cyclopentyl, cyclohexyl, 2-methylcyclopentyl, 3-methylcyclopentyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4
-Methylcyclohexyl group, 4-ethylcyclohexyl group, 4-n-propylcyclohexyl group, 4-isopropylcyclohexyl group, 4-tert-butylcyclohexyl group, etc., even when the ring is substituted with a C1-C4 alkyl group. Good C4 to C10 (cycloalkylalkyl) groups include, for example, cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, 1-cyclopropylethyl group, (2-methylcyclopropyl) methyl group, 2- (2-methylcyclopropyl) ethyl group, 2-cyclopentylethyl group,
A 3-cyclopentylpropyl group, a 2-cyclohexylethyl group, a 3-cyclohexylpropyl group, or the like, and a ring portion of which may be substituted with a C1-C4 alkyl group;
6 cycloalkenyl groups include, for example, 2-cyclopentenyl group, 3-cyclopentenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, 3,5,5-trimethyl-2-cyclohexenyl group, 3-methyl A C6-C8 (cycloalkenylalkyl) group which may be substituted with a C1-C4 alkyl group, for example, a (1-cyclopentenyl) methyl group, (2 -Cyclopentenyl) methyl group, (1-cyclohexenyl) methyl group, (2-cyclohexenyl)
Methyl group, (3-cyclohexenyl) methyl group, 2-
(3-cyclohexenyl) ethyl group and the like,

A halogen atom, a C1-C4 alkyl group, a C1-C3 represented by R ⁷ , R ¹⁵ , R ¹⁶ and R ⁴²
Haloalkyl group, C1-C3 alkoxy group or C1
To a phenyl group which may be substituted with a C3 haloalkoxy group, and a ring represented by R ⁷ , R ¹⁶ and R ⁴² , wherein the ring portion is a halogen atom, a C1-C4 alkyl group, a C1-C3 haloalkyl group, C3 alkoxy group or C1
The halogen atom in the benzyl group which may be substituted with a C3 haloalkoxy group is a fluorine atom, a chlorine atom,
A bromine atom or an iodine atom, and the C1-C4 alkyl group includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and tert.
-Butyl group or isobutyl group, and the C1-C3 haloalkyl group includes, for example, a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group, a 1-fluoroethyl group, a 1-chloroethyl group, a 1-bromoethyl group, Fluoroethyl group, 2-bromo-1,1,2,2
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, 2-chloropropyl group, 2-bromopropyl group, 2-iodopropyl group,
2,3-dibromopropyl group and the like, and the C1-C3 alkoxy group is a methoxy group, an ethoxy group, an n-propyloxy group or an isopropyloxy group,
The 3-haloalkoxy group is, for example, a trifluoromethoxy group, a bromodifluoromethoxy group, a 1-fluoroethoxy group, a 1-chloroethoxy group, a 1-bromoethoxy group, a perfluoroethoxy group, a 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-
Dibromopropyloxy group and the like,

The C5-C6 cycloalkylene group represented by E includes 1,2-cyclohexylene group, 1,3-cyclohexylene group, 1,4-cyclohexylene group,
A cyclopentylene group or a 1,3-cyclopentylene group, represented by R ⁶ , a cyano group, a nitro group, (C
The C1-C6 alkyl group which may be substituted with a 1-C4 alkoxy) carbonyl group, a C1-C4 alkylthio group or a C1-C4 alkoxy group includes, for example, a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group,
3-cyanopropyl group, nitromethyl group, 1-nitroethyl group, 1-methyl-1-nitroethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, isopropoxycarbonylmethyl group, 1- (methoxycarbonyl) ethyl group, 2- (Methoxycarbonyl) ethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2,2-dimethoxyethyl group, 2,2-diethoxyethyl group, 2,2-dimethoxypropyl group, 2,2-
Diethoxypropyl, 3,3-dimethoxypropyl, 3,3-diethoxypropyl, 2,3-dimethoxypropyl, methylthiomethyl, 2-methylthioethyl, 2,2-di (methylthio) ethyl And so on.

In a preferred embodiment of the compound of the present invention, a compound in which Y and Z are both oxygen atoms; a compound in which a is 0; R ¹ , R ² and R ³ each independently represent a halogen atom or C ¹ -C ³ Compounds that are alkyl groups;
A compound wherein A is A-1; a compound wherein A is A-2 and G ² is an oxygen atom; a compound wherein A is A-3 and Q ¹ is an oxygen atom; A is A-4 , Q ¹ and G ² are both oxygen atoms; a compound wherein A is A-5 and Q ¹ is an oxygen atom; a compound wherein A is A-6 and Q ¹ is an oxygen atom; G ¹ There compound is ^G 1 -1; is ^{G 1} is ^G 1 -2, compound ^{Q 2} is an oxygen atom; ^{R 6} is a hydrogen atom, C1 to C8 alkyl group, C2 -C6 haloalkyl group, C3 -C6 alkenyl A C3-C6 haloalkenyl group, a C3-C6 alkynyl group or a C3-C6 haloalkynyl group, or a C3-C7 cycloalkyl group optionally substituted with a C1-C4 alkyl group, or Wherein the ring is substituted with a C1-C4 alkyl group. A C4 to C10 (cycloalkylalkyl) group which may be substituted, or a C5 to C6 cycloalkenyl group which may be substituted by a C1 to C4 alkyl group; A C6-C8 (cycloalkenylalkyl) group which may be substituted with a group, or more preferably a C6-C8 (cycloalkenylalkyl) group.
1-C8 alkyl group, C2-C6 haloalkyl group, C3
A compound in which W is a benzene ring, or a 6-membered heterocyclic ring containing at least one oxygen atom, sulfur atom or nitrogen atom, or oxygen A compound which is a 5-membered heterocyclic ring containing at least one atom, sulfur atom or nitrogen atom, or in which these rings are substituted by 1 to 4 identical or different R ⁴⁰ . (R ⁴⁰ is a halogen atom, a C1-C4 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group or a C1-C3 haloalkoxy group. W is a benzene ring, a pyridine ring,
Pyridazine ring, pyrimidine ring, pyrazine ring, furan ring,
A thiophene ring, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a pyrazole ring or an imidazole ring, or these rings are 1 to 4 identical or different R ⁴⁰ ) (R
⁴⁰ has the same meaning as described above. An oxime-based compound substituted with W), wherein W is a benzene ring, a pyridine ring or a pyridazine ring, or these rings have 1 to 4 identical or different R ^{40 s} (R ⁴⁰ has the same meaning as described above.) Wherein W is a furan ring, a thiophene ring or a pyrrole ring, or these rings have from 1 to 3 identical or different R
An oxime compound substituted with ⁴⁰ (R ⁴⁰ has the same meaning as described above); W represents a benzene ring, a 2,3-pyridinediyl group, a 2,4-pyridinediyl group, a 2,5-pyridinediyl group , 2,6-pyridinediyl, 3,5-pyridinediyl, 3,4-pyridinediyl, 3,4-
A pyridazinediyl group, a 3,5-pyridazinediyl group or a 3,6-pyridazinediyl group, or a ring in which 1 to 4 identical or different R ⁴⁰ (R
⁴⁰ has the same meaning as described above. An oxime-based compound substituted by R) and R ² and R ³ are each independently a halogen atom or a C1-C3 alkyl group, and R ⁴ is 3,3-
A dichloro-2-propenyl group, a is 0,
And Z are both oxygen atoms, R ⁶ is a C1-C8 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group or a C3-C6 haloalkenyl group, and A is A
-1, G ¹ is G ¹ -1, (a1) is 0, W is a 1,3-phenylene group or a 1,4-phenylene group, h and p are both 0, R ¹⁹ ,
A compound wherein R ²⁰ , R ²⁵ , R ²⁶ , R ²⁹ and R ³⁰ are all hydrogen atoms; R ² and R ³ are each independently a halogen atom or a C1-C3 alkyl group, and R ⁴ is 3,3- A dichloro-2-propenyl group, a is 0, Y and Z are both oxygen atoms, and R ⁶ is C1-C
8 alkyl groups, C2-C6 haloalkyl groups, C3-C6
Alkenyl group or C3~C6 haloalkenyl group, A is an A-2, ^{G 1} is ^G 1 -1, (a
1) is 0, G ² is an oxygen atom, and W is 1,3-
A phenylene group or a 1,4-phenylene group, h and p are both 0, and R ¹⁹ , R ²⁰ , R ²⁵ ,
A compound wherein R ²⁶ , R ²⁹ and R ³⁰ are all hydrogen atoms. (Note that each symbol in the text has the same meaning as described above unless otherwise specified.)

Among the compounds of the present invention, particularly preferred compounds include (51) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-sec-butyl Oxime (36) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-tert-butyloxime (77) 4- (2- (2,6 -Dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-sec-butyloxime (79) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde.O-allyloxime (80) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde O- (3,3-dichloro-2-
Propenyl) oxime (60) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propoxy) benzaldehyde-On-propyloxime (61) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propoxy) benzaldehyde.O-isopropyloxime (62) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propoxy) benzaldehyde / O-sec-butyloxime (13) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propoxy) benzaldehyde-O-tert-butyloxime (15) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propoxy) acetophenone.O-ethyloxime (40) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propoxy) propiophenone.O-ethyloxime (19) 4 '-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butoxy) acetophenone.O-ethyloxime (32) 4 '-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butoxy) acetophenone-On-propyloxime (37) 4- (4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butoxy) benzaldehyde / O-isopropyloxime (242) 4 '-(3- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propoxy) -2,2,2-trifluoroacetophenone / O-ethyloxime. (Each number indicates the compound number of the present invention described below.)

[0013] Among the intermediate compounds represented by the formula (7), representative compounds are as follows: 1) 4-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) ) Phenoxy) methyl) benzaldehyde 17) 4 ′-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)
Acetophenone 18) 4- (2- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde 21) 4- (3- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde 33) 4 '-(2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone. (Each number indicates an intermediate compound number described later.) Also, among the intermediate compounds represented by the formula (8), 4) 4- (3- (2,6-dichloro) -4- (3,3-Dichloro-2-propenyloxy) phenoxy) propoxy) benzaldehyde 5) 4- (4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) Butoxy) benzaldehyde 6) 4 '-(3- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propoxy) acetophenone 7) 4 '-(4- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butoxy) acetophenone 11) 4 '-(3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propoxy) propiophenone 13) 4- (5- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde 14) 4 '-(5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) acetophenone 34) 4 '-(3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propoxy) -2,2,2-trifluoroacetophenone 35) 4 '-(4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butoxy) -2,2,2-trifluoroacetophenone 36) 4 '-(5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) -2,2,2-trifluoroacetophenone 37) 4 '-(4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butoxy) propiophenone 38) 4 '-(5- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) propiophenone 39) 4 '-(4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butoxy) benzophenone 40) 4 '-(5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) benzophenone. (Each number indicates an intermediate compound number described below.) Further, among the intermediate compounds represented by the formula (9), 4-((2,6-dichloro-4- ( 3,3-dichloro-
2-propenyloxy) phenoxy) methyl) benzaldehyde oxime 4 '-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl) acetophenone oxime 4- (2- ( 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde oxime 4 '-(2- (2,6-dichloro-4- (3,3-dichloro-2) -Propenyloxy) phenoxy) ethyl) acetophenone oxime 4- (3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propoxy)
Benzaldehyde oxime 4- (4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butoxy) benzaldehyde oxime 4- (5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde oxime 4 '-(3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propoxy ) Acetophenone oxime 4 '-(4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butoxy)
Acetophenone oxime 4 '-(5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) acetophenone oxime 4'-(3- (2,6-dichloro -4- (3,3-Dichloro-2-propenyloxy) phenoxy) propoxy) -2,2,2-trifluoroacetophenone oxime 4 '-(4- (2,6-dichloro-4- (3,3 -Dichloro-2-propenyloxy) phenoxy) butoxy)
-2,2,2-trifluoroacetophenone oxime 4 '-(5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) -2,2,2 -Trifluoroacetophenone oxime 4 '"-(3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propoxy) propiophenone oxime 4'-(4- ( 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butoxy)
Propiophenone oxime 4 '-(5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) propiophenone oxime 4'-(3- (2 4,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propoxy) benzophenone oxime 4 '-(4- (2,6-dichloro-4- (3,3-dichloro-2- Propenyloxy) phenoxy) butoxy)
Benzophenone oxime 4 '-(5- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzophenone oxime.

The compound of the present invention can be produced, for example, by the following (Production Method A) to (Production Method J). (Production method A) (Method for producing the compound of the present invention wherein R ⁶ is not a hydrogen atom) Formula (10) [Wherein, R ¹ , R ² , R ³ , R ⁶ , R ⁷ , A, a, Y and Z represent the same meaning as described above. However, compounds in which R ⁶ is a hydrogen atom are excluded. A compound of formula (11) L-R ⁴ wherein represented by], R ⁴ are as defined above, L is a halogen atom (e.g., chlorine atom, bromine atom, an iodine atom), mesyloxy or Represents a tosyloxy group. And a halide compound represented by the following formula: The above reaction is preferably performed in the presence of a base in an inert solvent. Examples of the solvent include ketones such as acetone, methyl ethyl ketone and cyclohexanone, 1,2-dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (for example, C _1-
C ₄ ) ethers (eg, diethyl ether, diisopropyl ether, etc.), polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile, nitromethane, dichloromethane, chloroform,
Examples thereof include halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, hydrocarbons such as toluene, benzene, and xylene, water, and a mixed solvent thereof. 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 alkoxide (for example, C ₁ -C ₄ ), triethylamine, pyridine and the like can be mentioned. Also, if necessary,
A catalyst such as an ammonium salt (eg, triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mol based on 1 mol of the compound represented by the formula (10). 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 raw material and the base to be used for the reaction can be arbitrarily set, but it is advantageous to carry out the reaction in an equimolar or close ratio. After completion of the reaction, the compound of the present invention can be isolated by performing ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound can be further purified by operations such as chromatography, distillation, and recrystallization. (Production Method B) (A method for producing a compound of the present invention in which Y is an oxygen atom and R ⁶ is not a hydrogen atom.) Among the compounds represented by the formula (10), compounds wherein Y is an oxygen atom (12) HO—R ⁴ [wherein, R ⁴ represents the same meaning as described above. A method of reacting with an alcohol compound represented by the formula: The above reaction is preferably carried out in the presence of a dehydrating agent, if necessary, in an inert solvent. Examples of the dehydrating agent include dicyclohexylcarbodiimide, dialkyl (for example, C ₁ -C ₄ ) azodicarboxylate (diethylazizocarboxylate,
Diisopropyl azodicarboxylate) -trialkyl (ex. C ₁ -C ₂₀ ) phosphine or triaryl phosphine (triphenyl phosphine, trioctyl phosphine, tributyl phosphine, etc.). Examples of the solvent include hydrocarbons such as benzene, xylene, and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene. Can be The reaction temperature is from -20 ° C to 200
It can be in the range of ° 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 compound of the present invention can be isolated by performing ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production Method C) (A method for producing a compound of the present invention wherein Y and Z are both oxygen atoms and R ⁶ is not hydrogen atom.) Formula (13) [Wherein, R ¹ , R ² , R ³ , R ⁴ and a represent the same meaning as described above. And a compound represented by the formula (14) [Wherein, R ⁶ , R ⁷ , A and L represent the same meaning as described above. And R ⁶ is not a hydrogen atom. The above reaction is preferably performed in the presence of a base in an inert solvent. As the solvent,
Ketones such as acetone, methyl ethyl ketone and cyclohexanone, ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (for example, C ₁ -C ₄ ) ether (for example, diethyl ether and diisopropyl ether), N, N- Polar solvents such as dimethylformamide, dimethylsulfoxide, 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 the like and a mixed solvent thereof are exemplified. 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,
Alkali metal or alkaline earth metal carbonates such as sodium carbonate and calcium carbonate, alkali metal or alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, sodium methoxide, sodium Ethoxide, potassium te
Examples thereof include alkali metal alkoxides (eg, C ₁ -C ₄ ) such as rt-butoxide, and organic bases such as triethylamine and pyridine. If necessary, a catalyst such as an ammonium salt (eg, triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mol based on 1 mol of the compound represented by the formula (13). Good. The reaction temperature can usually range from -20 ° C to the boiling point of the solvent used in the reaction or 150 ° C, but from -5 ° C to the boiling point of the solvent used in the reaction or 100 ° C.
Temperatures up to ° C are more desirable. The molar ratio of the raw material and the base to be used for the reaction can be arbitrarily set, but it is advantageous to carry out the reaction in an equimolar or close ratio. After completion of the reaction, the compound of the present invention can be isolated by performing ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound can be further purified by operations such as chromatography, distillation, and recrystallization. (Production Method D) (A method for producing a compound of the present invention in which both Y and Z are oxygen atoms and R ⁶ is not a hydrogen atom.) [Wherein, R ⁶ , R ⁷ and A represent the same meaning as described above. ]
A method of reacting a compound represented by the formula with a compound wherein R ⁶ is not a hydrogen atom. The above reaction is preferably carried out in the presence of a 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 _{2 0)} phosphine or triarylphosphine (triphenylphosphine, trioctylphosphine,
Tributylphosphine) and the like.
As the solvent, for example, benzene, xylene, hydrocarbons such as toluene, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane or carbon tetrachloride, dichloromethane, chlorobenzene,
And halogenated hydrocarbons such as dichlorobenzene. 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 compound of the present invention can be isolated by performing ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production Method E) A hydroxylamine compound represented by the formula (16) 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 (17) (Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁷ , A, Y, Z and a have the same meanings as described above). The above reaction is carried out in an inert solvent, if necessary, in the presence of a base or an acid. 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, and mixed solvents thereof. 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 alkoxide (for example, C ₁ -C ₄ ), triethylamine, pyridine and the like can be mentioned. It is preferable that the reaction is carried out by using at least 1 mol of a base used as necessary with respect to 1 mol of the hydroxylamine-based compound represented by the above formula (16). By carrying out the reaction using the hydroxylamine-based compound represented by (16) in a large excess, the role of the base and the solvent can also be achieved. Examples of the acid include hydrochloric acid, sulfuric acid, p
-Toluenesulfonic acid and the like;
7) The catalytic amount (0.
(01 to 1 equivalent). The hydroxylamine-based compound represented by the formula (16) can be used in the reaction as it is, but is usually used in the form of an inorganic acid salt such as hydrochloride and sulfate. The reaction temperature is from −20 ° C. to the boiling point of the solvent used for the reaction or 15 ° C.
The range can be up to 0 ° C, but usually the range is preferably from 0 ° C to the boiling point of the solvent used in the reaction or up to 60 ° C. The molar ratio of the raw materials and the reagents to be subjected to the reaction can be arbitrarily set, but the carbonyl compound of the formula (17) and the hydroxylamine compound of the formula (16) or a salt thereof are equimolar or a ratio close thereto. It is preferred to carry out the reaction. After completion of the reaction, the reaction solution was extracted with an organic solvent,
The compound of the present invention can be isolated by performing ordinary post-treatment operations such as concentration. The compound is obtained by chromatography,
Further purification can be performed by operations such as distillation and recrystallization. (Process F) ^{(R 6} is a hydrogen ^{atom, T 1 -4, T 1 -5} ,
T ¹ -6 and preparation of compounds that are not ^T 1 -7. .) Equation ⁽¹⁸⁾ R 6 -L (wherein, among the compounds represented by ^{R 6} and L represent the same meanings as defined above), ^{R 6} is a hydrogen ^{atom, T 1 -4,} T 1 -
^5, T 1 ^-6, not a ^T 1 -7 and ^T 1 -8 compound of formula (19) (Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁷ , A, Y, Z and a have the same meanings as described above). The above reaction is preferably performed in the presence of a base in an inert solvent. As the solvent, acetone, methyl ethyl ketone, ketones such as cyclohexanone,
1,2-dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (for example, C ₁ -C ₄ ) ether (for example, diethyl ether, diisopropyl ether, etc.)
Polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; Examples thereof include hydrocarbons such as toluene, benzene and xylene, water and the like, and mixed solvents thereof. 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 Alkoxide (for example, C _1-
And organic bases such as C ₄ ), triethylamine, pyridine and the like. If necessary, a catalyst such as an ammonium salt (for example, triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mol based on 1 mol of the compound represented by the formula (19). Good. 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 raw material and the base to be used for the reaction can be arbitrarily set, but it is advantageous to carry out the reaction in an equimolar or close ratio. After completion of the reaction, the compound of the present invention can be isolated by performing ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

(Production method G) (Production method of the compound of the present invention, wherein Y and Z are oxygen atoms, A is A-2, (e1) is 0, and R ⁶ is not a hydrogen atom. Equation (20) [Wherein R ¹ , R ² , R ³ , R ⁴ , R ¹⁹ , R ²⁰ , R
²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R
^{29, R 30, L, a} , h, j, p, u and v are as defined above. And a compound of formula (21) [Wherein R ⁶ , R ⁷ , G ¹ and W represent the same meaning as described above, Q ⁴ represents an oxygen atom, a sulfur atom or an NR ³⁹ group, and R ³⁹ represents a hydrogen atom or a C1-C3 alkyl group. A method of reacting with the compound represented by the formula The above reaction is preferably performed in the presence of a base in an inert solvent.
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, dimethyl ether, diisopropyl ether, etc.), N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, acetonitrile,
Examples thereof include polar solvents such as nitromethane, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene, hydrocarbons such as toluene, benzene and xylene, water, and mixed solvents thereof. 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 or alkalis such as lithium carbonate, sodium carbonate, potassium 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; and organic bases such as triethylamine and pyridine And the like.
If necessary, an ammonium salt (for example,
Catalyst such as triethylbenzylammonium chloride) in an amount of 0.01 to 1 mol of the compound represented by the formula (20).
It may be added in a proportion of about 1 mol. The reaction temperature is usually-
It can range from 20 ° C to the boiling point of the solvent used in the reaction or 150 ° C. The molar ratio of the raw material and the base to be used for the reaction can be arbitrarily set, 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,
The compound of the present invention can be isolated. The compound can be further purified by operations such as chromatography, distillation, and recrystallization. ^{R 6} in (Production Method K) (present compound ^T 1 -4,
Preparation of T ¹ -5 or ^T 1 -7, compound. Expression (22) (Wherein, J and ^{R 15} are as defined above, ^{L 1} is a chlorine atom or a bromine atom.) (For compounds ^{wherein R 6} is ^T 1 -4) a compound represented by or formula (2
3) (For compounds ^{wherein R 6} is ^T 1 -4) ^{(wherein, R 15} are as defined above.) Acid anhydride represented by or formula (24) (For compounds ^{wherein R 6} is ^T 1 -5) ^(wherein, L ^{1, J, R 16} and ^{R 42} are as defined above.) The compound represented by or formula (25) ^{(Wherein, R 15} and ^{L 1} are as defined above.) Sulfonyl halide compound represented by the (when ^{R 6} of the compound is ^T 1 -7), the compound represented by the formula (19) How to react. The above reaction is performed in an inert solvent in the presence of a base. Examples of the solvent include ketones such as acetone, methyl ethyl ketone, and cyclohexanone;
Ethers such as dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (for example, C ₁ -C ₄ ) ether (for example, diethyl ether, diisopropyl ether, etc.), N, N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulfolane , Acetonitrile, polar solvents such as nitromethane,
Examples include halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene, hydrocarbons such as toluene, benzene, and xylene, and mixed solvents thereof. 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-
Organic bases such as C ₄ ), triethylamine and pyridine are exemplified, 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 set arbitrarily, but the formula (1)
The reaction is carried out using 1 to 5 moles of each of the compound represented by the formula (22), the formula (23), the formula (24) or the formula (25) and the base with respect to 1 mol of the compound represented by the formula 9). Is advantageous. After completion of the reaction, the reaction solution was extracted with an organic solvent,
The compound of the present invention can be isolated by performing ordinary post-treatment operations such as concentration. The compound is obtained by chromatography,
Further purification can be performed by operations such as distillation and recrystallization.

(Production Method I) (R ^{6 in the} compound of the present invention)
There preparation of compounds that are ^T 1 -6. Isocyanate compound or isothiocyanate compound represented by the formula (26) R ¹⁶ -N = C = J (wherein J and R ¹⁶ represent the same meaning as described above), and a compound represented by the formula (19) How to react with. The reaction is carried out, if necessary, in the presence of a catalyst.
Performed in an inert solvent. Examples of the solvent include ketones such as acetone, methyl ethyl ketone, and cyclohexanone;
Ethers such as 2-dimethoxyethane, tetrahydrofuran, dioxane, dialkyl (for example, C ₁ -C ₄ ) ether (for example, diethyl ether, diisopropyl ether, etc.), N, N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, Polar solvents such as sulfolane, acetonitrile, and nitromethane;
Examples include halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene, hydrocarbons such as toluene, benzene, and xylene, and mixed solvents thereof. 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 etherate 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, but is 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 was extracted with an organic solvent,
The compound of the present invention can be isolated by performing ordinary post-treatment operations such as concentration. The compound is obtained by chromatography,
Further purification can be performed by operations such as distillation and recrystallization. (Production Method J) (In the compound of the present invention, R ⁶ is tert-
A method for producing a compound that is a butyl group. A method of reacting isobutene (CH ₂ ＣC (CH ₃ ) ₂ ) with the compound represented by the general formula (19). The above reaction is performed in an inert solvent in the presence of an acid catalyst. Examples of the solvent include hydrocarbons such as toluene, benzene, and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene, 1,2-dimethoxyethane, and tetrahydrofuran.
Examples include ethers such as dioxane and dialkyl (for example, C ₁ -C ₄ ) ether (for example, diethyl ether and diisopropyl ether), and esters such as ethyl acetate. If necessary, a mixed solvent of these solvents can be used. As the acid catalyst, for example,
Inorganic acids such as hydrochloric acid, hydrobromic acid, perchloric acid, sulfuric acid, nitric acid, phosphoric acid, or trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, etc. Organic acids are mentioned, and among them, sulfuric acid is preferred. The reaction temperature is -50
The temperature can be in the range of from 0 ° C. to 50 ° C. or the boiling point of the solvent used in the reaction, but is usually in the range of 0 ° C. to 30 ° C. The molar ratio of the raw materials to be used for the reaction can be arbitrarily set, but the reaction is preferably carried out using 1 mol or more of isobutene per 1 mol of the compound represented by the formula (19). After completion of the reaction, the compound of the present invention can be isolated by performing ordinary post-treatment operations such as extraction with an organic solvent and concentration.
The compound can be further purified by operations such as chromatography, distillation, and recrystallization.

Among the compounds of the present invention, when the compound has an asymmetric carbon atom, the compound of the present invention is an optically active isomer having a biological activity ((+)-isomer, (-)-isomer).
) And mixtures thereof in all ratios. In the case of the compounds of the present invention having geometrical isomerism, the compounds of the present invention have the respective biologically active geometrical isomers (cis And trans forms) and mixtures thereof in all proportions. Next, specific examples of the compound of the present invention are shown in Chemical formula 1 (Chemical 1-1 to Chemical 1-124), but the compound of the present invention is not limited thereto.

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In the chemical formula 1, (R ¹ ) _a , R ² , R ³ and M ₂ represent those described in Table 1 below, and R ⁶ represents the one described in Tables 2 to 19. ｝

[Table 1]

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Next, a method for producing an intermediate for producing the compound of the present invention will be described. The symbols in each scheme are
Unless otherwise specified, it has the same meaning as described above. The compound represented by the formula (10), which is an intermediate for producing the compound of the present invention, can be produced, for example, according to Schemes I to VI.

[Scheme I]

[Scheme II]

[Scheme III]

[Scheme IV]

[Scheme V] (Method for producing compound wherein R ⁶ is not a hydrogen atom.) (Wherein, TBDMSCl represents tert- butyldimethylsilyl chloride, ^{Z 1} represents an oxygen atom or a sulfur atom.)

[Scheme VI] (Method for producing compound in which R ⁶ is not a hydrogen atom.)

Formula (1) which is an intermediate for producing the compound of the present invention.
The compound represented by 3) can be produced, for example, according to Scheme VII. [Scheme VII]

Formula (1) which is an intermediate for producing the compound of the present invention.
As the halide compound represented by the formula (1) and the alcohol compound represented by the formula (12), commercially available ones can be used. Org. Chem. , 56,1037-104
1 (1991); Izvest. Akad. Nauk
S. S. S. R. , Otdel. Khim. Nauk,
1960, 447-451 [Chemical Abstract v
ol54, 22344d]; Doklady Aka
d. Nauk S.D. S. S. R. 132,606-60
8 (1960) [Chemical abstract vol 54,
22331h] or the like, or according to the following Scheme VIII.

[Scheme VIII] (Wherein, ^{L 1} represents a chlorine atom or a bromine atom, ^{L 2}
Represents a mesyloxy group or a tosyloxy group. )

Formula (1) which is an intermediate for producing the compound of the present invention.
As the compound represented by 6), a commercially available compound can be used, or it can be produced, for example, according to the following Scheme IX. [Scheme IX] (Method for producing compound wherein R ⁶ is not a hydrogen atom.) Wherein, ^{L 3} is a leaving group (e.g., halogen atom, hydroxy sulfonyloxy group, 2,4,6-trimethylbenzene sulfonyl group) ^{represents, R 103} and R
¹⁰⁴ represents a C1-C3 alkyl group, and other symbols have the same meanings as described above. However, the case where R ⁶ is a hydrogen atom is excluded. ]

Formula (2) which is an intermediate for producing the compound of the present invention.
2), Equation (23), Equation (24), Equation (25), and Equation (2)
The compound represented by 6) can be a commercially available compound, can be produced by a known method, or can be produced according to the method described below. [Compound of the formula (22) wherein J is a sulfur atom] Or
g. Chem. , 30, 1284 (1965); [Compound of the formula (24), wherein J is an oxygen atom] Am. Ch
em. Soc. , 81, 714 (1959); [Formula (3)
5) The compound wherein J is a sulfur atom] Justus Li
ebigs Ann. Chem. , 590, 123 (1
954)

Formula (1), which is an intermediate for producing the compound of the present invention,
The compounds represented by 4) and the formula (15) can be produced, for example, according to Scheme X. [Scheme X]

The compound represented by the formula (27) is, for example,
It can be produced according to Schemes XI-1 to XI-9. (Scheme XI-1) (In the case where G ¹ is G ^1-2 ) (Wherein, R ¹⁰¹ represents L or Q ⁴ H, Q ⁴ represents an oxygen atom, a sulfur atom or an NR ³⁴ group, R ³⁴ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,
¹⁰² for example represents the alcohol protecting group such as benzoyl group, ^{A 1} is the formula ^{(28) A 1 -1 :-( CR} 19 R 20) t - (CR 23 = CR
_{^{24) h - (CR 25 R}} 26) u - (CR 27 = CR
_{^{28) p - (CR 29 R}} 30) j - A 1 -2: -G 2 - (CR 19 R 20) j - (CR 23
_{^{= CR 24) h - (CR}} 25 R 26) u - (CR 27 =
_{^{CR 28) p - (CR 29}} R 30) v - A 1 -3 :-( CR 19 R 20) t - (CR 23 = CR
_{^{24) h - (CR 25 R}} 26) j -Q 1 - (CR 27 R
_{^{28) v - (CR 29 =}} CR 30) p - (CR 3 1 R
_{^{32) w - A 1 -4:}} -G 2 - (CR 19 R 20) j - (CR 23
_{^{= CR 24) h - (CR}} 25 R 26) v -Q 1 - (CR
_{^{27 R 28) w - (CR}} 29 = CR 30) p - (CR
_{^{31 R 32) x - A 1}} -5 :-( CR 19 R 20) t -Q 1 - (CR 23
_{^{R 24) h -E- (CR 25}} R 26) p - A 1 -6 :-( CR 19 R 20) t -Q 1 - (CR 23
_{^{R 24) j -C≡C- (CR 25}} R 26) m - represents, and other symbols are as defined above. )

[Scheme XI-2] (When A is A-3)

[Scheme XI-3] (In the case where A is A-5)

[Scheme XI-4] (When A is A-6)

[Scheme XI-5] (When A is A-2)

[Scheme XI-6] (When A is A-4)

[Scheme XI-7] (When A is A-5 and t is 0)

[Scheme XI-8] (In the case where A is A-6 and t = 0)

[Scheme XI-9] (When A is A-4) (In the formula, Q ⁵ represents an oxygen atom, a sulfur atom or an NR ³³ group.)

Formula (2) which is an intermediate for producing the compound of the present invention.
The compound represented by 0) can be produced, for example, according to Scheme XII. [Scheme XII]

Formula (2) which is an intermediate for producing the compound of the present invention.
The compound represented by 1) can be produced, for example, according to Scheme XIII. [Scheme XIII] (In the formula, Q ⁷ represents an oxygen atom or a sulfur atom.)

Formula (1) which is an intermediate for producing the compound of the present invention.
As the compound represented by 8), a commercially available compound can be used, or it can be produced, for example, according to the following scheme XIV. [Scheme XIV]

Formula (1) which is an intermediate for producing the compound of the present invention
The carbonyl compound represented by 7) can be produced, for example, according to Schemes XV-1 to XV-5. [Scheme XV-1]

[Scheme XV-2] (In the case where A is A-2 and Y and Z are oxygen atoms)

[Scheme XV-3] (R ⁷ = H, W = W
^{1, A = A-2,} G 1 = G 1 -1, (a1) = 0, Y =
(In the case where Z is an oxygen atom) (Wherein, R ¹⁰⁵ represents a methyl group or an ethyl group;
¹ represents a benzene ring or a hetero ring having no -NH- group in the ring. )

[Scheme XV-4] (R ⁷ = H, W = W
^{1, A = A-2,} G 1 = G 1 -1, (a1) = 0, Y =
(In the case where Z is an oxygen atom) (Wherein, R ¹⁰⁸ represents a methyl group or an ethyl group,
Alternatively, two R ¹⁰⁸ are bonded at the terminal to each other to represent an ethylene group or a trimethylene group. )

[Scheme XV-5] (R ⁷ = H, A = A
−1, G ¹ = G ¹ −1, (a1) = 0, W = W ¹ , t =
h = u = p = 0, j = 1, R ²⁹ = R ³⁰ = H, Y = Z
= In the case of a compound that is an oxygen atom)

Formula (1) which is an intermediate for producing the compound of the present invention.
The compound represented by 9) can be produced, for example, according to Scheme XVI. [Scheme XVI]

Formula (29), Formula (30) or Formula (31)
Some of the compounds represented by are commercially available compounds, or are represented by the following schemes XVII-1 to XV:
It can be manufactured according to II-4. [Scheme XVII-1] (Wherein, R ¹⁰⁶ represents a methyl group or an ethyl group;
¹⁰⁷ is an alkyl group having 1 to 6 carbon atoms, 3 to 6 carbon atoms
Or a cycloalkyl group of 1 to 4 carbon atoms
Represents a phenyl group or a benzyl group which may be substituted with an alkyl group or an alkoxy group having 1 to 3 carbon atoms. )

[Scheme XVII-2]

[Scheme XVII-3]

[Scheme XVII-4]

The schemes XV-3, XV-4, XV
-5, Formula (35) used in XVII-1, XVII-2, XVII-3 and XVII-4: R ¹⁰⁹ -W ¹ -R ¹¹⁰ (wherein R ¹⁰⁹ and R ¹¹⁰ are L ¹ , Q ⁴ H , CH
O, CH (OR ¹⁰⁸ ) ₂ , CO ₂ H, CO
₂ R ¹⁰⁵ , COCH ₃ or CH ₂ L ¹ , and other symbols have the same meanings as described above. The compound represented by the formula (1) can be commercially available or can be produced, for example, according to the method described in the following literature. Compounds in which W ¹ is a pyridazine ring: J. Hetero
cyclic Chem. , 5, 845 (196
8): Monatscheft fur Che
m. , 110, 365 (1979) and the like. Compound in which W ¹ is a pyrimidine ring: Justus Li
ebigs Ann. Chem. , 684, 209
(1965): J. Heterocyclic C
hem. , 28, 1281 (1991): Che.
m. Ber. , 97, 3407 (1964):
J. Chem. Soc. , 1965, 546
7: Aust. J. Chem. , 19, 232
1 (1966) and the like. Compounds in which W ¹ is a pyrazine ring: J. Org. Ch
em. , 54, 640 (1089) and the like. Compounds in which W ¹ is an oxazole ring: Org.
Chem. , 57, 4797 (1992). Compound in which W ¹ is an isoxazole ring: Chem.
Pharm. Bull. , 14, 92 (196
6): Chem. Pharm. Bull. , 14,
1277 (1966): Chem. Pharm.
Bull. , 19, 46 (1971): J. C
hem. Res. Synop. , 1994, 11
6: Synthesis, 1976, 992 and the like. Compounds in which W ¹ is a thiazole ring: Am. Ch
em. Soc. , 72, 5221 (1950)
etc. Compounds wherein W ¹ is an isothiazole ring: Che
m. Soc. , 1959, 3061 and the like. Compound in which W ¹ is an imidazole ring: Tetrahed
ron Lett. , 26, 1915 (1985)
etc. Compound in which W ¹ is a pyrazole ring: Chem. Be
r. , 112, 1712 (1979): Che.
m. Ber. , 116, 1520 (198
3): JP-A-63-185964: Tetrahedr
on, 29, 441 (1973): J. Am. Che
m. Soc. Chem. Commun. , 19
69, 66: J Org. Chem. , 35,
3451 (1970): Chem. Ber. , 1
03, 2356 (1970) and the like.

Examples of the harmful insects and harmful mites to which the compound of the present invention has control effect include the following. Hemiptera pests: brown planthopper (Laodelfax)
striatellus), brown planthopper (Nila)
parvata lugens)
hoppers, such as G. galella furcifera),
Black leafhopper (Nephotettix cinc)
ticeps), Leafhopper (Empo)
leafhoppers such as asca onukii), aphids such as cotton aphid (Aphis gossypiii) and peach aphid (Myzus persicae), stink bugs, and whitefly (Triale)
urodes vapororiorum, Bemisiatabaci, Silverleaf whitefly (Bemisia argentifo)
lii) and other whiteflies, scale insects, firebugs, psyllids, etc. Lepidopteran pests: Chilo suppres
salis), Kobumemeiga (Cnaphalocro)
cis medicinalis), European corn borer (Ostrinia nubilalis), Shibattoga (Parapediasia terre)
llla) and other Japanese moths such as Spodop
terura litura), Spodoptera litura (Sp)
podoptera exigua), armyworm (Ps)
eudaletia separata, armyworm (Mamestra brassicae), amanita moth (Agrotis ipsilon), genus Trichoplusia spp., genus Heliotis sp., Helioa sp. Species, Pieris brassicae (Pieris rapae crucivor)
a) and other white butterflies,
oxophies orana fasciata),
Nasihime Shingui (Grapholita moles)
ta), codling moss (Cydia pomonel)
la) etc., and peach sink moth (Carpos)
Singing moths such as ina nipponensis, and peach squirrel
a) and the like, Phyllonono
lyctor ringoniella, etc .;
italella, etc., and moth moth (Plu)
Suga such as Tella xylostella, pink ball worm (Pectinophoragossy)
piella), Diptera pests such as houseflies, mosquitoes, anopheles, chironomids, houseflies, blowflies, sarcophagids, flies, flies, flies, and flies. , Drosophila, Drosophila, Flyes, Blackflies, Dermatophagoides, etc. Coleopteran pests: Chrysomelids, Scarabaeids, Weevil, Beetles, Ladybirds, Cerambycidae, Beetles, etc. Thrips: Thrips palmiformes
ps palmi), thrips of the citrus yellow thrips (Frankliniella occide)
ntalis, etc., Frankliniella spp., Thrips thrips dorsal
is) and other thrips and thrips of the genus Siltthrips, etc. Hymenoptera tree pests: wasps, ants, wasps, etc. Reptile pests: cockroaches, German cockroaches, etc. Orthoptera pests: grasshoppers, Pteridophytes, etc. Laminariae pests: Human fleas, etc. Pests of louse: Lice, etc. Termites pests: Termites, etc. Mites pests: Tetranychus
spp. ), Panonychus
spp. ) Etc., spider mites, dust mites, Fucus 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, it is usually used as a solid carrier, liquid carrier, gaseous carrier, or the like. Mix with feed, etc., and add surfactants and other auxiliaries for formulation as needed, oils, emulsions, wettable powders, flowables such as suspensions in water and emulsions in water, granules, powders ,
Formulated into aerosols, aerosols (eg, fogging), bait, microcapsules, etc. for use. These preparations usually contain the present compound as an active ingredient in an amount of 0.01% to 95% by weight.

Examples of solid carriers used in the preparation include, for example, 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.) and fine powders or granules such as chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, salt ammonium, etc.). Water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (hexane, cyclohexane,
Kerosene, light 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.), dimethyl sulfoxide, vegetable oils such as soybean oil and cottonseed oil, and the like. Freon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas and the like can be mentioned.
Examples of the surfactant include an alkyl sulfate salt,
Examples thereof include alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. Examples of pharmaceutical auxiliaries such as fixing agents and dispersants include 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.), and as a stabilizer, for example, PAP
(Acidic isopropyl phosphate), BHT (2,6-di-t)
tert-butyl-4-methylphenol), BHA (2
-Tert-butyl-4-methoxyphenol and 3-t
tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids or esters thereof, and the like.

Flowable preparations such as suspensions in water and emulsions in water generally contain 1 to 75% by weight of the active ingredient compound in 0.5% by weight.
１５15% by weight of a suspending aid (for example, a protective colloid or a substance capable of imparting thixotropic properties), 0 to 10% by weight of a auxiliaries (eg, an antifoaming agent, a rust inhibitor, a stabilizer, a spreading agent, a penetration aid) Agents, antifreezing agents, preservatives, fungicides, etc.) in water. By using an oil in which the active ingredient compound hardly dissolves in place of water, a suspension in oil can be obtained. Examples of the protective colloid include gelatin, casein, gums, cellulose ethers, and polyvinyl alcohol. Examples of the substance capable of imparting thixotropic properties include bentonite, aluminum magnesium silicate, xanthan gum, and polyacrylic acid. The microencapsulating agent is an interfacial polymerization method, In-S
It can be prepared by an itu method, a phase separation method, a submerged drying method, a spray drying method, a melting dispersion cooling method, a pan coating method and the like. For example, in the interfacial polymerization method, 1 to 50
If necessary, 0.001 to 1% by weight of an oil-soluble monomer is dissolved in an organic solvent that does not dissolve in water, and 0.001 to 5% of a surfactant or a water-soluble polymer is added. Then, a microencapsulation agent can be prepared by reacting at 30 to 80 ° C. for 1 to 48 hours. Thereafter, if necessary, a suspending aid (eg, a protective colloid or a substance capable of imparting thixotropic properties) or an auxiliary (eg, an antifoaming agent, a rust inhibitor, a stabilizer, a spreading agent, a penetration aid,
Antifreezing agents, preservatives, fungicides, etc.) can also be added. Examples of the film material of the microcapsule by the interfacial polymerization method include a polyamide using a polybasic acid halide as an oil-soluble monomer, a polyamide using a polyamine as a water-soluble monomer, and a polybasic acid halide as an oil-soluble monomer. Polyester using polyphenol as a monomer, polyurethane using an isocyanate as an oil-soluble monomer, and using a polyol as a water-soluble monomer can be exemplified.

Examples of the bait bait 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. And the like, and attractant flavors such as cheese flavor, onion flavor and the like. The preparation thus obtained is used as it is or diluted with water or the like. Also other pesticides,
They 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.

Examples of such insecticides, nematicides and acaricides include, 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-methylpyrimidin-4-yl phosphorothioate], chloropyrifos [O, O-diethyl-O-
3,5,6-trichloro-2-pyridyl phosphorothioate], acephate [O, S-dimethylacetyl phosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,3 4-thiadiazol-3-ylmethyl O, O-dimethylphosphorodithioate], disulfoton [O, O-diethyl
S-2-ethylthioethyl phosphorothioate], DD
VP [2,2-dichlorovinyldimethyl 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-benzodioxaphosphinin-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)], profenophos [O-
4-bromo-2-chlorophenyl O-ethyl S-propyl phosphorothioate].
BPMC (2-sec-butylphenylmethylcarbamate), 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-
Methyl carbamate], Methomil [S-methyl-N-
[(Methylcarbamoyl) oxy] thioacetimidate], ethiophenecarb [2- (ethylthiomethyl)
Phenylmethyl carbamate], 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-{[methyl (1-methylthioethylideneaminooxycarbonyl) amino] thio}
Carbamate-based compounds such as -β-alaninato] and etofenprox [2- (4-ethoxyphenyl) -2]
-Methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS) -α-cyano-3-
Phenoxybenzyl (RS) -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 (1
RS, 3RS) -3- (2,2-dichlorovinyl)-
2,2-dimethylcyclopropanecarboxylate],
Permethrin [3-phenoxybenzyl (1RS, 3R
S) -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], cyfluthrin [cyano (4-fluoro-3-phenoxyphenyl) methyl 3- (2,2-dichloroethenyl)-
2,2-dimethylcyclopropanecarboxylate] and its isomer, cycloprosulin [(RS) -α-cyano-3-phenoxybenzyl (RS) -2,2-dichloro-1- (4-ethoxyphenyl) cyclo Propanecarboxylate], fluvalinate (α-cyano-3-phenoxybenzyl N- (2-chloro-α, α, α-trifluoro-p-tolyl) -D-valinate), bifenthrin (2-methylbiphenyl-3) -Ylmethyl)
(Z)-(1RS) -cis-3- (2-chloro-3,
3,3-trifluoroprop-1-enyl) -2,2-
Dimethylcyclopropane carboxylate, acrinathrin ([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-thiadiazinan-4-one), nitroimidazolidine derivatives, acetamiprid [(E) -N1-((6-chloro-3-pyridyl) methyl) -N2-cyano-N1 -Methylacetamidine], cartap [S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate)], thiocyclam [N,
Neraistoxin derivatives such as N-dimethyl-1,2,3-trithian-5-ylamine] and bensultap [S, S'-2-dimethylaminotrimethylene di (benzenethiosulfonate)]; acetamiprid [N- N-cyanoamidine derivatives such as cyano-N'-methyl-N '-(6-chloro-3-pyridylmethyl) acetamidine] and 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
Chlorinated hydrocarbon compounds such as 5,6-hexachlorocyclohexane) and 1,1-bis (chlorophenyl) -2,2,2-trichloroethanol;
-(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-
Benzoylphenylurea-based compounds such as chloro-4-trifluoromethylphenoxy) -2-fluorophenyl) -3- (2,6-difluorobenzoyl) urea]
Amitraz [N, N '-[(methylimino) dimethylidinyl] di-2,4-xylysine], chlorodimform [N'-(4-chloro-2-methylphenyl) -N, N
-Dimethylmethinimidamide], thiourea derivatives such as diafenthiuron [N- (2,6-diisopropyl-4-phenoxyphenyl) -N'-tert-butylcarbodiimide], bromopropylate [ Isopropyl 4,4'-dibromobenzylate], tetradiphone [4-chlorophenyl 2,4,5
-Trichlorophenyl sulfone], quinomethionate [S, S-6-methylquinoxaline-2,3-diyldithiocarbonate], propargate [2- (4-te
rt-butylphenoxy) cyclohexyl prop-2
-Yl sulfite], fenbutatin oxide [bis [tris (2-methyl-2-phenylpropyl)]
Tin] oxide], hexthiazox [(4RS, 5
RS) -5- (4-Chlorophenyl) -N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], clofentezine [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], tebufenpyrado [N-4-tert-butylbenzyl] -4-chloro-
3-ethyl-1-methyl-5-pyrazolecarboxamide], polynactin complex [tetranactin,
Dinactin, Trinactin], Milbemectin, Avermectin, Ivermectin, Emamectin benzoate azadirachtin [AZAD], Pyrimidiphene [5-chloro-N- [2-Δ4- (2-ethoxyethyl) -2,3]
-Dimethylphenoxydiethyl] -6-ethylpyrimidin-4-amine, chlorfenapyr [4-bromo-2-
(4-chlorophenyl) -1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile], tebufenidide [N-tertbutyl-N '-(4-ethylbenzoyl) -3,5-dimethylbenzohydrazide], Phenylpyrazole derivative, spinosad, indoxacarb [indeno (1,2-e) (1,3,4)
Oxadiazine-4a (3H) -carboxylic acid, 7-chloro-2,5-dihydro-2-(((methoxycarbonyl) (4-trifluoromethoxyphenyl) amino) carbonyl)-, methyl ester] and the like. .

When the compound of the present invention is used as an insecticide or acaricide for agriculture, the application rate is usually 0.1 g to 100 g per 10 ares. And the like are diluted with water, the application concentration is usually 1 ppm to 10000 p.
pm, and granules, powders and the like are applied as they are without dilution. When used as an insecticide for insect control or acaricide, emulsions, wettable powders, flowables, microcapsules, etc. are usually 0.1 ppm to 500 ppm in water.
diluted to ppm and applied, oils, aerosols, aerosols,
For poison bait, etc., apply as it is. These application rates,
The application concentration varies 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.

[0206]

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 (1) by Production Example 1 (Production Method D) 0.35 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, 4- (hydroxymethyl) benzaldehyde.O- 0.25 g of diisopropyl azodicarboxylate was slowly added dropwise to a mixture of 0.32 g of (3,3-dichloro-2-propenyl) oxime, 0.32 g of triphenylphosphine and 10 ml of dichloromethane while stirring under ice-cooling. . After stirring at room temperature for 12 hours, the reaction solution was concentrated to obtain a residue. This residue was subjected to silica gel chromatography,
4-((2,6-dichloro-4- (3,3-dichloro-
2-propenyloxy) phenoxy) methyl) benzaldehyde O- (3,3-dichloro-2-propenyl)
0.43 g of the oxime was obtained. Yield 67% mp 76.
2 ° C. Production of compound (15) by Production Example 2 (Production Method E) 4 ′-(3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone (Prepared in Intermediate Production Example 2) A mixture of 0.31 g and 10 ml of pyridine was added with O-
After adding 0.07 g of ethylhydroxylamine 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 to obtain a crude product. The crude product was subjected to silica gel chromatography to give 4 '-(3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-ethyloxime 0.33 g was obtained. Yield 99% n _D
^24.5 1.5948

Compound (2) according to Production Example 3 (Production Method E)
Preparation of 5) 0.21 g of 3- (3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde and 10 ml of pyridine
To a mixture of O-ethylhydroxylamine hydrochloride 0.1.
After adding 09 g and 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 to give a crude product. The crude product was subjected to silica gel chromatography to give 3- (3- (2,2
0.21 g of 6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde.O-ethyloxime was obtained. Yield 9
2% mp 42.6 ° C Production of compound (75) by Production Example 4 (Production Method E) 4- (2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) Ethyl) benzaldehyde (prepared in Production Example 3 of Intermediate described below) 0.5
0.18 g of O-propylhydroxylamine hydrochloride was added to a mixture of 5 g of pyridine and 5 ml of pyridine, and the mixture was stirred at room temperature for 24 hours. The combined ethyl ether layers were washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-propyloxime 0.45
g was obtained. Yield 72% _n ^D 24.5 1.5773

Compound (8) according to Production Example 5 (Production Method E)
Production of 6) 5-acetyl-2- (3- (2,6-dichloro-4-)
0.17 g of O-ethylhydroxylamine hydrochloride was added to a mixture of 0.43 g of (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) pyridine and 10 ml of pyridine, and the mixture was stirred at room temperature for 24 hours. The solution was poured into dilute hydrochloric acid and extracted twice with diethyl ether. The combined ethyl ether layers were washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 5- (1-
(N-ethoxyimino) ethyl) -2- (3- (2,6
-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) pyridine 0.4
0 g was obtained. Yield 89% _n ^D 24.5 1.570
1 Production of Compound (91) by Production Example 6 (Production Method E) 4- (3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde 0.43 g Then, 0.15 g of O-tert-butylhydroxylamine hydrochloride was added to a mixture of 5 ml of pyridine and stirred at room temperature for 24 hours, and then 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 to give a crude product. This crude product was subjected to silica gel chromatography to give 4- (3-
0.38 g of (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde / O-tert-butyloxime was obtained. Yield 75% _n ^D 25.5 1.5673

Compound (20) obtained in Production Example 7 (Production Method D)
Production of 3) 0.62 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, 5- (hydroxymethyl) -2-furfural.O- (3,3-dichloro-2) To a mixture of 0.54 g of -propenyl) oxime, 0.57 g of triphenylphosphine and 10 ml of dichloromethane, 0.44 g of diisopropyl azodicarboxylate was slowly added dropwise with stirring under ice cooling.
After stirring at room temperature for 12 hours, the reaction solution was concentrated to obtain a residue. This residue was subjected to silica gel chromatography,
5-((2,6-dichloro-4- (3,3-dichloro-
0.43 g of 2-propenyloxy) phenoxy) methyl) -2-furfural.O- (3,3-dichloro-2-propenyl) oxime was obtained. Yield 69% mp6
5.0 ° C

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) phenoxymethyl) benzaldehyde O- (3,3-dichloro-2-propenyl) oxime Melting point 76.2 ° C (2) 4- (2,6-dichloro-4- (3,3-dibromo-2-) Propenyloxy) phenoxymethyl) benzaldehyde O- (3,3-dichloro-2-propenyl) oxime Melting point 88.2 ° C (3) 4- (2- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde O- (3,3-dichloro-2-
Propenyl) oxime Melting point 88.0 ° C (4) 4- (2- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde O- (3,3-dibromo-2-
Propenyl) oxime melting point 90.8 ° C (5) 4- (3- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde.O- (3,3-dichloro-2-propenyl) oxime n _D ^24.5 1.58
72 (6) 4- (3- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde O- (3,3-dibromo-2-propenyl) oxime n _D ^24.5 1.58
52 (7) 4- (4- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde O- (3,3-dichloro-
2-propenyl) oxime n _D ^24.5 1.581
9 (8) 4- (4- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde O- (3,3-dibromo-
2-propenyl) oxime n _D ^24.5 1.594
1 (9) 4- (2- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde.O-ethyloxime n _D
^21.5 1.5760 (10) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-ethyloxime
n _D ^21.5 1.5664 (11) 4- (4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-ethyloxime n _D
^21.5 1.5613 (12) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde / O-tert-butyloxime n _D ^21.5 1.5628 (13) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-tert-butyloxime n _D ^21.5 1.5588 (14) 4- (4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-tert-butyloxime n _D ^21.5 1.5528 (15) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone / O-ethyloxime
n _D ^24.5 1.5948 (16) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-tert-butyloxime n _D ^24.5 1.5949 (17) 4 '-(3- (2,6-dichloro-4- (3 ,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O- (3,3-dichloro-2-propenyl) oxime n _D ^24.5 1.5
950 (18) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O- (3,3-dibromo-2-propenyl) oxime n _D ^24.5 1.5
943 (19) 4 '-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) acetophenone · O-ethyloxime Melting point 41.9 ° C (20) 4 ′-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) acetophenone / O-tert-butyloxime melting point 56.4 ° C (21) 4 '-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) acetophenone.O- (3,3-dichloro-2-propenyl) oxime n _D ^24.5 1.57
85 (22) 4 '-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) acetophenone.O- (3,3-dibromo-2-propenyl) oxime n _D ^24.5 1.59
09 (23) 3- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-methyloxime
n _D ^24.5 1.5802 (24) 3- (4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-methyloxime n
_D ^24.5 1.5756 (25) 3- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-ethyloxime
Melting point 42.6 ° C (26) 3- (4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-ethyloxime n
_D ^24.5 1.5723 (27) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-methyloxime
n _D ^24.5 1.5871 (28) 4- (4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-methyloxime Melting point 63.5 ° C (29) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone / O-methyloxime
n _D ^22.5 1.5642 (30) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-propyloxime n _D ^22.5 1.5733 (31) 4 '-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) acetophenone.O-methyloxime n
_D ^22.5 1.5686 (32) 4 '-(4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) acetophenone / O-propyloxime
n _D ^22.5 1.5589 (33) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-methyloxime melting point 95.9 ° C (34 ) 4- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde O- (2-propenyl) oxime
75.6 ° C (35) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde · O-benzyloxime Melting point 70.3
° C (36) 4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde.O-tert-butyloxime n _D
^24.5 1.5713 (37) 4- (4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde-O-iso-propyloxime n _D ^24.5 1.5643 (38) 4- (4- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-iso-butyloxime n _D ^24.5 1.5571 (39) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) benzophenone / O-ethyloxime
^{_{n D 24.5 1.5943 (40) 4}} '- (3- (2,6- dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) propiophenone-O-ethyloxime melting point 42.4 ° C (41) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) valerophenone / O-ethyloxime
n _D ^24.5 1.5535 (42) 4- (5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde / O-ethyloxime
n _D ^24.5 1.5730 (43) 4 '-(5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) acetophenone / O-ethyloxime
Melting point: 56.1 ° C. (44) 4 ′-(2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethyloxy) acetophenone.O-ethyloxime n
_D ^24.5 1.5840 (45) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde O- (3,3-dichloro-2-propenyl) ) oxime ^{_{n D 24.0 1.6006 (46) 3-}} (2,6- dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde · O-benzyl-oxime n _D ^22.5
1.6095 (47) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-tert-butyloxime n _D
^23.0 1.5753 (48) 4- (2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-ethyloxime Melting point 84.8 ° C (49) 4 -(2,6-Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-propyloxime Melting point 45.4
° C

(50) 4- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde · O-isopropyloxime n _D ^24.0 1.5858 (51) 4- (2,6-dichloro-4- (3,3-dichloro-) 2-propenyloxy) phenoxy) methylbenzaldehyde / O-sec-butyloxime Melting point 5
9.6 ° C (52) 3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-allyloxime Melting point 63.9 ° C (53) 3- ( 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylbenzaldehyde / O-sec-butyloxime n _D
^24.5 1.5783 (54) 4 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) propiophenone oxime melting point 1
40.0 ° C (55) 4- (5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde oxime melting point 90.
1 ° C. (56) 4 ′-(5- (2,6-dichloro-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) pentyloxy) acetophenone oxime melting point 79.
5 ° C (57) 3- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde oxime n _D
^24.0 1.5640 (58) 3 '-(3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) valerophenone oxime melting point 87.
0 ° C. (59) 4 ′-(2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) acetophenone oxime melting point 121.0
° C (60) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde-O-propyloxime n _D ^24.5 1.5703 (61) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde-O-isopropyloxime n _D ^24.5 1.5653 (62) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde-O-sec-butyloxime n _D ^24.5 1.5665 (63) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-iso-butyloxime n _D ^24.5 1.5579 (64) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-allyloxime
n _D ^24.5 1.5990 (65) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde-O-benzyloxime n _D ^24.5 1.5886 (66) 4 '-(2,6-dichloro-4- (3,3-dichloro-2) -Propenyloxy) phenoxy) methylacetophenone.O- (3,3-dichloro-2-propenyl) oxime n _D ^25.0 1.5965 (67) 4 '-(2,6-dichloro-4- (3,3 -Dichloro-2-propenyloxy) phenoxy) methylacetophenone.O-methyloxime n _D ^26.5
1.5947 (68) 4 '-(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylacetophenone.O-propyloxime n _D ^26.0
1.5808 (69) 4 '-(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylacetophenone.O-propyloxime n _D ^26.0
1.5904 (70) 4 '-(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylacetophenone / O-tert-butyloxime n _D
^25.5 1.5717 (71) 4 '-(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylacetophenone.O-ethyloxime n _D ^26.0
1.5865 (72) 4 '-(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methylacetophenone.O-benzyloxime n _D ^26.5
1.6655 (73) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-methyloxime n _D
^24.5 1.5921 (74) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-ethyloxime n _D
^24.5 1.5846 (75) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-propyloxime n _D
^24.5 1.5773 (76) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde-O-iso-propyloxime n _D ^24.5 1.5762 (77) 4- (2- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-sec-butyloxime
n _D ^25.0 1.5718 (78) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde-O-tert-butyloxime n _D ^26.0 1.5669 (79) 4- (2- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-allyloxime n _D
^26.0 1.5849 (80) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde O- (3,3-dichloro-2-
Propenyl) oxime n _D ^26.5 1.5932 (81) 4- (2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-benzyloxime n _D
^27.0 1.5967 (82) 2- (4- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) methyl) phenoxy) acetaldehyde.O-
(3,3-dichloro-2-propenyl) oxime melting point 87.9 ° C (83) 4- (2- (2,6-dichloro-4- (3,3
- dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde · O- (4-tert- butylbenzyl) oxime ^{_{n D 26.0 1.5818 (84) 4-}} (2- (2,6- dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde / O-cyclohexyloxime
^{_{n D 26.0 1.5685 (85) 4-}} (2- (2,6- dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde O- (3-phenylpropyl)
Oxime ^{_{n D 26.0 1.5902 (86) 1-}} (5- (2- (3- (2,6- dichloro -
4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) pyridyl)) acetaldehyde.O-ethyloxime n _D ^24.5 1.5701 (87) 4- (3- (2,6-dichloro) -4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde O-methyloxime n _D
^25.5 1.5876 (88) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde O-ethyloxime n _D
^26.0 1.5802 (89) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde O-propyloxime n _D
^25.5 1.5763 (90) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde-O-iso-propyloxime n _D ^25.5 1.5734 (91) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde-O-tert-butyloxime n _D ^25.5 1.5673 (92) 4- (3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde / O-allyloxime n _D
^25.5 1.5844 (93) 4- (3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde O- (3,3-dichloro-2
-Propenyl) oxime n _D ^25.0 1.5920 (94) 4 '-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) acetophenone / O-iso-propyloxime (95) 4 '-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) acetophenone / O-butyloxime (96) 4 '-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) acetophenone / O-iso-butyloxime (97) 4 '-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) acetophenone.O-sec-butyloxime (98) 4-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)
Benzaldehyde / O-butyl oxime (99) 3-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)
Benzaldehyde / O-methyl oxime

(100) 3-((2,6-dichloro-4)
-(3,3-dichloro-2-propenyloxy) phenoxy) methyl) benzaldehyde / O-ethyloxime (101) 3-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) benzaldehyde / O-propyloxime (102) 3-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) benzaldehyde / O-iso-propyloxime (103) 3-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) benzaldehyde / O-iso-butyloxime (104) 4- (3- (2,6-dichloro-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde / O-iso-butyloxime (105) 4- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde / O-sec-butyloxime (106) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde O- (3,3-dichloro-2
-Propenyl) oxime (107) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde.O-methyloxime (108) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde / O-ethyloxime (109) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde / O-propyloxime (110) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde-O-iso-propyloxime (111) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde / O-butyloxime (112) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde / O-iso-butyloxime (113) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde-O-sec-butyloxime (114) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde / O-tert-butyloxime (115) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
(3,3-dichloro-2-propenyl) oxime (116) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
Methyl oxime (117) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
Ethyl oxime (118) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
Propyloxime (119) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
iso-propyloxime (120) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
Butyl oxime (121) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
iso-butyloxime (122) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone.O-
sec-butyl oxime (123) 4 '-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) -2,2,2-trifluoroacetophenone o-
tert-butyl oxime (124) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone.O- (3,3-dichloro-2-propenyl) oxime (125) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone.O-methyloxime (126) 4 '-(2- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone.O-ethyloxime (127) 4 '-(2- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone.O-propyloxime (128) 4 '-(2- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone / O-iso-propyloxime (129) 4 '-(2- (2,6-dichloro-4 −
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone.O-butyloxime (130) 4 '-(2- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone / O-iso-butyloxime (131) 4 ′-(2- (2,6-dichloro-4) −
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone / O-sec-butyloxime (132) 4 '-(2- (2,6-dichloro-4) −
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone / O-tert-butyloxime (133) 4 '-(3- (2,6-dichloro-4) −
(3,3-dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone.O- (3,3-dichloro-2-propenyl) oxime (134) 4 '-(3- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propyl-trifluoroacetophenone.O-methyloxime (135) 4 '-(3- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone.O-ethyloxime (136) 4 '-(3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone.O-propyloxime (137) 4 '-(3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone / O-iso-propyloxime (138) 4 '-(3- (2,6-dichloro-4) −
(3,3-Dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone.O-butyloxime (139) 4 '-(3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone / O-iso-butyloxime (140) 4 '-(3- (2,6-dichloro-4) −
(3,3-dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone.O-sec-butyloxime (141) 4 '-(3- (2,6-dichloro-4) −
(3,3-dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone / O-tert-butyloxime (142) 4- (2- (2,6-dichloro-4-) (3,
3-Dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde.O-methyloxime (143) 4- (2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde / O-propyloxime (144) 4- (2- (2,6-dichloro-4- (3,
3-Dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde / O-iso-propyloxime (145) 4- (2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde · O-butyloxime (146) 4- (2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde / O-iso-butyloxime (147) 4- (2- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde / O-sec-butyloxime (148) 4- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde / O-butyloxime (149) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-propyloxime

(150) 4- (4- (2,6-Dichloro-4- (3,3-dichloro-3-propenyloxy) phenoxy) butyloxy) benzaldehyde.O-se
c-Butyl oxime (151) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-4-propenyloxy) phenoxy) butyloxy) benzaldehyde / O-butyloxime (152) 4- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde / O-methyloxime (153) 4- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde-O-propyloxime (154) 4- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde / O-iso-propyloxime (155) 4- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde / O-butyloxime (156) 4- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde / O-iso-butyloxime (157) 4- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde / O-sec-butyloxime (158) 4- (5- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde / O-tert-butyloxime (159) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde.O-methyloxime (160) 1- (2- (3- (2,6-dichloro-4-)
(3,3-Dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde.O-ethyloxime (161) 1- (2- (3- (2,6-dichloro-4-)
(3,3-Dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde.O-propyloxime (162) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde / O-iso-propyloxime (163) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde.O-butyloxime (164) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde / O-iso-butyloxime (165) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde.O-sec-butyloxime (166) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde.O-tert-butyloxime (167) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde.O- (3,3-dichloro-2-propenyl) oxime (168) 1- (2- (4- ( 2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-methyloxime (169) 1- (2- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-ethyloxime (170) 1- (2- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-propyloxime (171) 1- (2- (4- (2,6-dichloro-4-)
(3,3-Dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-iso-propyloxime (172) 1- (2- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-butyloxime (173) 1- (2- (4- (2,6-dichloro-4-)
(3,3-Dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-iso-butyloxime (174) 1- (2- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-sec-butyloxime (175) 1- (2- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O-tert-butyloxime (176) 1- (2- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde.O- (3,3-dichloro-2-propenyl) oxime (177) 2- (3- (2,6- Dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Methyloxime (178) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Ethyl oxime (179) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Propyloxime (180) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Iso-propyloxime (181) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Butyl oxime (182) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Iso-butyloxime (183) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Sec-butyloxime (184) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-Tert-butyloxime (185) 2- (3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl-phenyl-ketone-O
-(3,3-dichloro-2-propenyl) oxime (186) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
Methyl oxime (187) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
Ethyl oxime (188) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
Propyl oxime (189) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
iso-propyl oxime (190) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
Butyl oxime (191) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
iso-butyloxime (192) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
sec-butyl oxime (193) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
tert-butyl oxime (194) 2- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl-phenyl-ketone-O-
(3,3-dichloro-2-propenyl) oxime (195) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural.O-methyloxime (196) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural.O-ethyloxime (197) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural.O-propyloxime (198) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural.O-iso-propyloxime (199) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural O-butyloxime

(200) 5-((2,6-dichloro-4)
-(3,3-dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural • O-iso-butyloxime (201) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural O-sec-butyloxime (202) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural.O-tert-butyloxime (203) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural.O- (3,3-dichloro-2)
-Propenyl) oxime melting point 65.0 ° C (204) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophencarboxaldehyde.O-methyloxime (205) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophenecarboxaldehyde.O-ethyloxime (206) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophencarboxaldehyde.O-propyloxime (207) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophenecarboxaldehyde O-is
o-Propyl oxime (208) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophenecarboxaldehyde.O-butyloxime (209) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophenecarboxaldehyde O-is
o-Butyl oxime (210) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophenecarboxaldehyde O-se
c-Butyl oxime (211) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophenecarboxaldehyde O-te
rt-butyloxime (212) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-thiophencarboxaldehyde O-
(3,3-dichloro-2-propenyl) oxime (213) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde.O-methyloxime (214) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde.O-ethyloxime (215) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde.O-propyloxime (216) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde O-iso
-Propyloxime (217) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde.O-butyloxime (218) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde O-iso
-Butyloxime (219) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde O-sec
-Butyl oxime (220) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde O-ter
t-butyl oxime (221) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-pyrrolecarboxaldehyde O- (3
3-dichloro-2-propenyl) oxime (222) 5-((2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) methyl) -2-furfural.O- (3,3-dibromo-2)
-Propenyl) oxime (223) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone.O-methyloxime n _D
^26.0 1.5816 (224) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone.O-ethyloxime n _D
^26.0 1.5772 (225) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone / O-propyloxime n
_D ^28.0 1.5732 (226) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone.O-tert-butyloxime n _D ^27.5 1.5559 (227) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone.O-allyloxime n _D
^25.5 1.5828 (228) 4 '-(2- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone.O- (3,3-dichloro-2-propenyl) oxime n _D ^25.0 1.59
06 (229) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde O-methyloxime n _D
^26.5 1.5802 (230) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde O-ethyloxime n _D
^26.5 1.5744 (231) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde / O-propyloxime n _D
^26.5 1.5708 (232) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde-O-tert-butyloxime n _D ^26.5 1.5624 (233) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde O-allyloxime n _D
^26.5 1.5794 (234) 4- (4- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde O- (3,3-dichloro-2
-Propenyl) oxime n _D ^26.5 1.5856 (235) 3 '-(3- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-methyloxime n _D ^25.5 1.5786 (236) 3 '-(3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-ethyloxime n _D ^26.0 1.5717 (237) 3 '-(3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-propyloxime n _D ^25.0 1.5692 (238) 3 '-(3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-isopropyloxime n _D ^25.0 1.5656 (239) 3 '-(3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-sec-butyloxime n _D ^25.0 1.5606 (240) 3 '-(3- (2,6-dichloro-4) −
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O-tert-
Butyl oxime n _D ^25.0 1.5580 (241) 4 '-(3- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -2,2,2-trifluoroacetophenone oxime (242) 4 '-(3- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -2,2,2-trifluoroacetophenone.O-ethyloxime (243) 4 '-(6- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) hexyloxy) acetophenone.O-ethyloxime (244) 4 '-(3- (2,6-dichloro-4-
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone.O- (1,1,
1,3,3,3-hexafluoroisopropyl) oxime

Next, a production example of the carbonyl compound represented by the formula (17) will be shown. Intermediate Production Example 1 Production of Intermediate Compound 1) Terephthalaldehyde 2.06 g of ethanol 20 ml
While stirring under ice-cooling, 0.15 g of sodium borohydride was slowly added. After stirring at room temperature for 12 hours, ethanol was distilled off. Pour the residue into diluted hydrochloric acid,
The mixture was extracted with ethyl acetate, the ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product.
This crude product was subjected to silica gel chromatography,
1.06 g of p- (hydroxymethyl) benzaldehyde
Was obtained (51% yield). 3.40 g of p- (hydroxymethyl) benzaldehyde obtained in the same manner, 7.2 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, and triphenylphosphine 6.
To a mixture of 56 g and 50 ml of tetrahydrofuran, 5.05 g of diisopropyl azodicarboxylate was slowly added dropwise with stirring under ice cooling. After stirring at room temperature for 12 hours, the reaction solution was concentrated to obtain a residue. The residue was subjected to silica gel chromatography to give 4-((2,
6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl) benzaldehyde
75 g were obtained. Yield 46%; mp 93.9 ° C Intermediate Production Example 2 Production of Intermediate Compound 6) 10.0 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenol, 1,3 14.0 g of -dibromopropane and 50 ml of N, N-dimethylformamide were put into a reaction vessel, 5.3 g of potassium carbonate was added to the reaction solution, and the mixture was stirred at room temperature for 12 hours, and then filtered. The filtrate was poured into diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed twice 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 1- (3-bromopropyloxy) -2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) benzene 6.1 g
I got (Yield 43%) 1- (3-bromopropyloxy)-obtained by the same method.
0.56 g of potassium carbonate was added to a solution of 1.50 g of 2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) benzene and 0.50 g of p-hydroxyacetophenone in 30 ml of N, N-dimethylformamide. ,
After stirring at room temperature for 24 hours, the reaction solution was poured into dilute hydrochloric acid,
Extracted twice with diethyl ether. The combined ethyl ether layers were washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, and 1.51 g of 4 '-(3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone was obtained.
I got Yield 89% mp 73.6 ° C

Intermediate Preparation Example 3 Preparation of Intermediate Compound 18) 15.67 g of 4-bromophenethyl alcohol, 3,4
6.88 g of dihydro-2H-pyran, catalytic amounts of p-toluenesulfonic acid monohydrate and tetrahydrofuran 10
0 ml of the mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water and extracted twice with 100 ml of diethyl ether. The diethyl ether layers were combined, washed successively with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and concentrated under reduced pressure to give 4- (2- (2-
21.5 g of tetrahydropyranyloxy) ethyl) -1-bromobenzene were obtained. Yield 97% mp 93.9
C. A mixture of 11.3 g of 4- (2- (2-tetrahydropyranyloxy) ethyl) -1-bromobenzene and 100 ml of tetrahydrofuran was cooled to -78.degree.
6M n-butyllithium / n-hexane solution 25.9
ml was added dropwise over 15 minutes. After stirring at −78 ° C. for 1 hour, N, N-dimethylformamide 4.2 was added at the same temperature.
ml was added dropwise over 15 minutes. Furthermore, at -78 ° C, 1
After stirring for an hour, saturated ammonium chloride aqueous solution 100m
1 was added and stirring was continued until the temperature reached room temperature. Reaction mixture 2
The mixture was extracted twice with 00 ml of ethyl acetate, the ethyl acetate layers were combined, washed three times with a saturated aqueous solution of ammonium chloride, and then washed with saturated saline. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a residue. This residue was subjected to silica gel column chromatography to give 4-
7.20 g of (2- (2-tetrahydropyranyloxy) ethyl) benzaldehyde was obtained. Yield 78% n _D
^24.5 1.5311 4- (2- (2-tetrahydropyranyloxy) ethyl) benzaldehyde 6.50 g, acetone 130 ml
And 110 ml of 1M hydrochloric acid was stirred at room temperature for 24 hours. The reaction mixture was neutralized by adding a saturated aqueous solution of sodium bicarbonate, and extracted twice with 200 ml of ethyl acetate. The ethyl acetate layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography to obtain 3.88 g of 4- (2-hydroxyethyl) benzaldehyde. Yield 93% ¹ H-NMR (CDCl ₃ / TMS) δ (ppm):
1.42 to 1.88 (6H, m), 2.99 (2H,
t) 3.42-3.49 (1H, m), 3.60-
3.74 (2H, m), 3.94-4.04 (1H,
m) 4.58-4.60 (1H, m), 7.38-
7.43 (2H, m), 7.79 to 7.84 (2H,
m), 9.98 (1H, s)

3.88 g of 4- (2-hydroxyethyl) benzaldehyde, 2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenol 6.7
g, 100 ml of tetrahydrofuran and 6.0 g of triphenylphosphine, 4.7 g of diisopropyl azodicarboxylate in 20 ml of tetrahydrofuran at an ice temperature.
Was added dropwise over 1 hour. After dropping,
After stirring at room temperature for 24 hours, the reaction mixture was concentrated under reduced pressure,
The obtained residue was subjected to silica gel column chromatography to give 4- (2- (2,6-dichloro-4- (3,3-
6.63 g of dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde were obtained. 69% yield
mp 54.2 ° C Intermediate Production Example 4 Production of Intermediate Compound 20) 1- (3-Bromopropyloxy) -2,6-dichloro-4- (3, obtained by the method described in Intermediate Production Example 3. 3-dichloro-2-propenyloxy) benzene 11.1 g,
3.31 g of benzoic acid and 50 ml of N, N-dimethylformamide were placed in a reaction vessel, and 3.9 of potassium carbonate was added thereto.
After adding 0 g and stirring at room temperature for 24 hours, the reaction solution was poured into water and extracted twice with diethyl ether. The combined ethyl ether layers were washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. The crude product was subjected to silica gel chromatography to give 3,5-dichloro-4
-(3-benzoyloxypropyloxy) -1-
11.6 g of (3,3-dichloro-2-propenyloxy) benzene was obtained (95% yield). This 3,5-dichloro-4- (3-benzoyloxypropyloxy) -1
11.6 g of-(3,3-dichloro-2-propenyloxy) benzene and 15.2 of a 10% aqueous potassium hydroxide solution
After stirring a solution of g in 300 ml of methanol at room temperature for 24 hours, the reaction solution was concentrated. The concentrate was poured into water and extracted twice with diethyl ether. The combined ethyl ether layers were washed with water, dried over anhydrous magnesium sulfate and concentrated.
A crude product was obtained. The crude product was subjected to silica gel chromatography to give 3- (2,6-dichloro-4- (3,
3-dichloro-2-propenyloxy) phenoxy)-
7.41 g of 1-propyl alcohol was obtained (yield 83
%). 3- (2,6-dichloro-4-) obtained in a similar manner.
(3,3-dichloro-2-propenyloxy) phenoxy) -1-propyl alcohol 2.00 g tert-
A solution of 20 ml of butyl methyl ether was stirred under ice cooling with sodium hydride (60% oil) 0.24.
g was added slowly. After 10 minutes, 5-acetyl-2-
0.9 g of chloropyridine (produced in Reference Production Example 1 described below)
Was added at room temperature for 1 hour, and then the internal temperature was adjusted to 80 using an oil bath.
Stirred at C for 5 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.
A crude product was obtained. This crude product was subjected to silica gel chromatography to give 5-acetyl-2- (3- (2,6-
Dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) pyridine 0.62
g was obtained. Yield 23% mp 90.5 ° C

Next, some specific examples of the carbonyl compound represented by the formula (17) will be shown together with the compound number and some of the physical properties. 1) 4-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl) benzaldehyde mp 93.9 ° C 2) 4-((2,6-dichloro-4-) (3,3-dibromo-2-propenyloxy) phenoxy) methyl) benzaldehyde 3) 4- (2- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) ethoxy) benzaldehyde mp 81.3 ° C 4) 4- (3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde mp 76.5 ° C 5) 4- (4 -(2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde mp 54.9 ° C 6) 4 '-(3 -(2,6-Dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxy) acetophenone mp 73.6 ° C 7) 4 '-(4- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxy) acetophenone glassy 8) 3- (3- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) benzaldehyde n _D ^24.5 1.580
9 9) 3- (4- (2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) benzaldehyde n _D ^24.5 1.5770 10) 4 '-(3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) benzophenone n _D ^24.5 1.59
28 11) 4 '-(3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) propiophenone mp 39.8 ° C 12) 4 '-(3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyloxy) valerophenone n _D ^24.5 1.57
03 13) 4- (5- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) pentyloxy) benzaldehyde mp 41.4 ° C. 14) 4 ′-(5- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) acetophenone mp 101.0 ° C 15) 4 '-(2- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) ethyloxy) acetophenone mp 100.1 ° C 16) 3-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl) benzaldehyde ¹ H-NMR (CDCl ₃ / TMS) δ (ppm): 4.61 (2H, d), 5.06 (2
H, s), 6.13 (1H, t), 6.89 (2H,
s), 7.58 (1H, t), 7.86 (1H, d
t), 7.87 (1H, dt), 8.05 (1H,
t) 10.06 (1H, s) 17) 4 '-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)
Acetophenone mp 88.6 ° C 18) 4- (2- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) ethyl) benzaldehyde mp 54.2 ° C 19) 2- (4-((2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) methyl) phenoxy) acetaldehyde 20) 5-acetyl-2- (3- (2,6-dichloro-)
4- (3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) pyridine mp 90.5 ° C 21) 4- (3- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyl) benzaldehyde mp 61.0 ° C 22) 4- (4- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyl) benzaldehyde 23) 4 '-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)
-2,2,2-trifluoroacetophenone 24) 4 '-(2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) -2,2,2-trifluoroacetophenone 25) 4 '-(3- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) propyl) -2,2,2-trifluoroacetophenone 26) 1- (2- (3- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridyl) acetaldehyde 27) 1- (2- (4- (2,6-dichloro-4-)
(3,3-dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridyl) acetaldehyde 28) 2- (3- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) propyloxy) -5-pyridylphenyl ketone 29) 2- (4- (2,6-dichloro-4- (3,3-
Dichloro-2-propenyloxy) phenoxy) butyloxy) -5-pyridylphenyl ketone 30) 5-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)-
2-furfural 31) 5-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)-
2-thiophenecarboxaldehyde 32) 5-((2,6-dichloro-4- (3,3-dichloro-2-propenyloxy) phenoxy) methyl)-
2-pyrrolecarboxaldehyde 33) 4 '-(2- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) ethyl) acetophenone mp 88.5 ° C 34) 4 '-(3- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) propoxy) -2,2,2-trifluoroacetophenone 35) 4 '-(4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butoxy) -2,2,2-trifluoroacetophenone 36) 4 '-(5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) -2,2,2-trifluoroacetophenone 37) 4 '-(4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butoxy) propiophenone 38) 4 '-(5- (2,6-dichloro-4- (3,3)
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) propiophenone 39) 4 '-(4- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) butoxy) benzophenone 40) 4 '-(5- (2,6-dichloro-4- (3,3
-Dichloro-2-propenyloxy) phenoxy) pentyloxy) benzophenone

Next, production examples of the intermediate compound represented by the general formula (10) will be shown. Intermediate Preparation Example 5 [Preparation of Intermediate Compound 45] 2,6-Dichloro-4-benzoyloxyphenol (This compound can be synthesized according to the method described in JP-A-8-337549) 2.83 g, 4- 2.74 g of (2-hydroxyethyl) benzaldehyde.O- (3,3-dichloro-2-propenyl) oxime, 2.62 g of triphenylphosphine and 40 m of tetrahydrofuran
A solution of 2.02 g of diisopropyl azodicarboxylate in 10 ml of tetrahydrofuran was slowly added dropwise to the mixture (1) while stirring at 0 ° C. under a nitrogen stream. After stirring at room temperature for 24 hours, the reaction mixture is concentrated under reduced pressure to obtain a residue. This residue was subjected to silica gel column chromatography to give 4- (2- (2,6-dichloro-
4-benzoyloxyphenoxy) ethyl) benzaldehyde.O- (3,3-dichloro-2-propenyl) oxime is obtained. To a solution of 5.39 g of 4- (2- (2,6-dichloro-4-benzoyloxyphenoxy) ethyl) benzaldehyde / O- (3,3-dichloro-2-propenyl) oxime in 20 ml of methanol was added 0
0.56 g of potassium hydroxide and 5 ml of water while stirring at ℃
The solution dissolved in is added dropwise. After stirring at room temperature for 3 hours,
The reaction solution is acidified by adding diluted hydrochloric acid, and concentrated under reduced pressure to obtain a residue. Water is added to the obtained residue, and the mixture is extracted twice with ethyl acetate. The ethyl acetate layers are combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. This crude product was subjected to silica gel column chromatography,
-(2- (2,6-dichloro-4-hydroxyphenoxy) ethyl) benzaldehyde.O- (3,3-dichloro-2-propenyl) oxime (intermediate compound 45)
Get.

Next, some specific examples of the carbonyl compound represented by the formula (10) will be shown together with the compound numbers. 41) 4- (2,6-Dichloro-4-hydroxyphenoxy) methylbenzaldehyde / O-sec-butyloxime 42) 4- (2,6-Dichloro-4-hydroxyphenoxy) methylbenzaldehyde / Ot-butyloxime 43) 4- (2- (2,6-dichloro-4-hydroxyphenoxy) ethyl) benzaldehyde-O-sec-
Butyl oxime 44) 4- (2- (2,6-dichloro-4-hydroxyphenoxy) ethyl) benzaldehyde / O-allyl oxime 45) 4- (2- (2,6-dichloro-4-hydroxyphenoxy) ethyl) Benzaldehyde O- (3,3
-Dichloro-2-propenyl) oxime 46) 4- (3- (2,6-dichloro-4-hydroxyphenoxy) propyloxy) benzaldehyde O-
n-propyloxime 47) 4- (3- (2,6-dichloro-4-hydroxyphenoxy) propyloxy) benzaldehyde.O-
Isopropyl oxime 48) 4- (3- (2,6-dichloro-4-hydroxyphenoxy) propyloxy) benzaldehyde O-
sec-butyl oxime 49) 4- (3- (2,6-dichloro-4-hydroxyphenoxy) propyloxy) benzaldehyde-O-
t-butyl oxime 50) 4 '-(3- (2,6-dichloro-4-hydroxyphenoxy) propyloxy) acetophenone.O-
Ethyl oxime 51) 4 '-(3- (2,6-dichloro-4-hydroxyphenoxy) propyloxy) propiophenone.O
-Ethyloxime 52) 4 '-(4- (2,6-dichloro-4-hydroxyphenoxy) butyloxy) acetophenone.O-ethyloxime 53) 4'-(4- (2,6-dichloro-4-hydroxyphenoxy) ) Butyloxy) acetophenone ・ On
-Propyloxime 54) 4- (4- (2,6-dichloro-4-hydroxyphenoxy) butyloxy) benzaldehyde / O-isopropyloxime 55) 4 '-(3- (2,6-dichloro-4-hydroxyphenoxy) Propyloxy) -2,2,2-trifluoroacetophenone / O-ethyloxime

Reference Production Example 1 (Production Example of 5-acetyl-2-chloropyridine used in Intermediate Production Example 4) 15.45 g of 6-chloronicotinic acid and 100 ml of diethyl ether were placed in a reaction vessel, and cooled with ice ( Internal temperature 0-5
C), 131 ml of methyllithium (1.5 M ether solution) was slowly added dropwise while stirring. After dropping,
Stir at room temperature. After 24 hours, the reaction solution was concentrated, the residue was poured into dilute hydrochloric acid, and extracted twice with diethyl ether. The combined ethyl ether layers were washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography to obtain 13.11 g of 5-acetyl-2-chloropyridine (yield: 8).
6%).

Next, a production example of the intermediate compound represented by the formula (16) will be shown. Reference Production Example 2 [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 in a mixture of 1,1,3-trichloro-1-propene 4 at room temperature.
After adding 1 g and stirring at room temperature for 12 hours, the reaction solution was poured into dilute hydrochloric acid to precipitate crystals. The crystals were collected by filtration, washed sequentially with water and hexane, and dried under reduced pressure to give N-
66 g of (3,3-dichloro-2-propenyloxy) phthalimide were 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, followed by heating under reflux. After stirring for 3 hours, the temperature was returned to room temperature and hexane 100
ml was added. 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. When hydrogen chloride gas is blown into the filtrate, crystals precipitate. The crystals are 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
(Ppm): 4.76 (2H, s), 6.17 (1H,
t)

Reference Production Example 3 [Production of O- (3- (5-trifluoromethyl-2-pyridyloxy) propyl) hydroxylamine] 12.6 g of 1,3-propanediol and 100 ml of N, N-dimethylformamide The mixture is placed under a stream of nitrogen,
While stirring, at room temperature, 3.30 g of 60% sodium hydride (oily) was added in portions over 30 minutes. Further, after stirring was continued at room temperature for 1 hour, 2-chloro-5 was added.
A solution of 10.0 g of trifluoromethylpyridine in 20 ml of N, N-dimethylformamide was added dropwise over 40 minutes. Furthermore, after continuing stirring at room temperature overnight, about 2N
Was added over 15 minutes to terminate the reaction. The obtained reaction solution was extracted twice with a total of 500 ml of toluene, and the combined toluene layers were washed successively with dilute hydrochloric acid and a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and concentrated to give 9.70 g of oil. I got something.
This oily substance was dissolved by heating in 300 ml of hexane and recrystallized to give 2- (3-hydroxypropyloxy)-.
5.3 g of 5-trifluoromethylpyridine were obtained. (Yield 44%, mp. 46.6 ° C) 2- (3-hydroxypropyloxy) -5-trifluoromethylpyridine 20.0 g, N-hydroxyphthalimide 14.7 g, triphenylphosphine 23.6
g and 200 ml of tetrahydrofuran, 20.0 g of diisopropylazodicarboxylate was slowly added dropwise with stirring under a nitrogen stream under ice cooling. After stirring at room temperature for 24 hours, the reaction solution was concentrated to obtain a residue. This residue was subjected to silica gel chromatography,
27.8 g of N- (3- (5-trifluoromethyl-2-pyridyloxy) propyloxy) phthalimide were obtained. (Yield 84%, mp. 97.6 ° C.) Hydrazine hydrate 1 was added to a mixture of 12.8 g of N- (3- (5-trifluoromethyl-2-pyridyloxy) propyloxy) phthalimide and 150 ml of chloroform at room temperature. A mixture of 0.74 g and 1.5 ml of isopropyl alcohol was slowly dropped, and 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 the filtrate was concentrated to obtain a residue.
Hexane (100 ml) was added again, 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-
(5- (trifluoromethyl) -2-pyridyloxy)
7.0 g of (propyl) hydroxylamine were obtained. yield
85% ¹ H-NMR (CDCl ₃ / TMS) δ (ppm):
2.08 (2H, q), 3.83 (2H, t), 4.4
4 (2H, t), 5.41 (2H, s), 6.79-
6.83 (1H, m), 7.74 to 7.78 (1H,
m), 8.42 to 8.44 (1H, m) Reference Production Example 4 [O- (2,2,2-trichloroethyl)
Production of hydroxylamine hydrochloride] 2.99 g of 2,2,2-trichloroethanol, O-
(2,4,6-trimethylbenzenesulfonyl) hydroxylamine [Synthesis, 1-17 (197
It was manufactured according to the method described in 7). ] 2.15 g
To a mixture of 20 ml of diethyl ether 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 / TMS) δ
(Ppm): 4.84 (2H, s) 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 present compounds (1) to (244) were dissolved in 35 parts of xylene and 35 parts of dimethylformamide.
Add polyoxyethylene styryl phenyl ether 1
4 parts and 6 parts of calcium dodecylbenzenesulfonate are added and mixed well with stirring to obtain each 10% emulsion. Formulation Example 2 wettable powder 20 parts of each of the compounds of the present invention (1) to (244) were mixed with 4 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of fine powder of synthetic hydrous silicon oxide and silicon earth 54.
Parts, mix well, stir and mix well and add 20%
Obtain wettable powder. Formulation Example 3 Granules To 5 parts of each of the compounds (1) to (244) of the present invention, 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 the mixture is sufficiently stirred and mixed. 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 compounds of the present invention (1) to (244) is dissolved in an appropriate amount of acetone.
, 0.3 parts of PAP and 93.7 parts of clay were added, mixed well with stirring, and the acetone was removed by evaporation to obtain 1% powder of each. Formulation Example 5 Flowable agent 20 parts of each of the present compounds (1) to (244) 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. (With a particle size of 3 μm or less)
40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate are added, and 10 parts of propylene glycol are further added and stirred and mixed to obtain a 20% flowable agent for each. Formulation Example 6 Oil agent 0.1 part of each of the present compounds (1) to (244) 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 (244) of the present invention, 10 parts of trichloroethane and 59.9 parts of deodorized kerosene were mixed and dissolved, and the mixture was filled in an aerosol container, and a valve was attached. After that, the propellant (liquefied petroleum gas) 30
The parts are pressurized to obtain the respective oily aerosols. Formulation Example 8 aqueous aerosol 0.2 part of each of the present compounds (1) to (244), 5 parts of xylene, 4.8 parts of deodorized kerosene, and an emulsifier @Atmos 30
0 (manufactured by Atlas Chemical Co.)｝ Aerosol container was filled with 1 part of mixed and dissolved water and 50 parts of pure water, and a valve was attached. Then, 40 parts of propellant (liquefied petroleum gas) was passed through the valve. Fill under pressure to obtain each aqueous aerosol. Formulation Example 9 Mosquito Incense Includes 0.3 g of each of the present compounds (1) to (244) in d-
0.3 g of allethrin was added and dissolved in 20 ml of acetone, and a carrier for mosquito coils (tab flour: lees flour: wood flour 4: 3: 3
After mixing uniformly with 99.4 g of water, 120 ml of water was added, and the mixture was kneaded well and then molded and dried to obtain each mosquito coil.

Formulation Example 10 Electric Mosquito Cat Mat 0.4 g of each of the present compounds (1) to (244), d-
Allesulin 0.3 g and piperonyl butoxide 0.4
Add acetone to g and dissolve 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 (244) 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 (244) is dissolved in 0.5 ml of acetone, and this solution is used as a solid feed powder for animals (solid feed powder for breeding and breeding, CE-2, CLEA Japan, Inc.). (Commodity) Process to 5g and mix evenly. The acetone is then evaporated to dryness to obtain each poison bait. Formulation Example 13 Microencapsulating agent Compound of the present invention (13), (15), (19), (3)
6), (37), (39), (40), (51), (7)
7) 1 g of (79), (80), 4.8 g of Sumidur L-75 and 200 g of Solvesso 200 were uniformly mixed and added to 175 g of a 10% by weight aqueous gum arabic solution containing 6 g of ethylene glycol. , T .; K. Using an auto homomixer, the mixture is dispersed and stirred at room temperature at 3500 rpm to obtain fine droplets. Subsequently, the mixture is gently stirred at 60 ° C. for 24 hours to obtain a microcapsule slurry in which the active ingredient compound is included in the polyurethane film. 2 g of xanthan gum and 4 g of aluminum silicate were added to the obtained slurry.
Is added to obtain a microencapsulating agent containing 0.1% by weight of the active ingredient.

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-phenoxy-benzaldehyde.O
-(3-methylbutyl) oxime [JP-A-61-260]
Compound 41 described on page 4 of JP-A-054

Test Example 1 [Spodoptera litura (Spodo)
Insecticidal Test Against Ptera litura) 13 g of artificial feed (Insector LF: 2 ml) of a 200-fold diluted solution (500 ppm) of the test compound preparation obtained in Preparation Example 1 or 2 with water in a polyethylene cup having a diameter of 11 cm. Made by Nippon Agricultural Products). 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 (93), (203) and (22)
3) to (244) each showed a mortality of 80% or more. In contrast, the mortality of the compound (A) was 0%. Test Example 2 [Pongella xylos
Insecticidal test on Tella)] A spreading agent (New Linow: Nippon Agrochemical Co., Ltd.) was added to a dilution (50 ppm) of the test compound preparation obtained in Preparation Example 1 with water at a dilution equivalent to 3000-fold, and the pot was added. The cabbage (fourth to fifth leaf stage) cultivated in the above was sprayed with 25 ml per pot. 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), (3), (5),
(7), (9) to (21), (23) to (35), (3)
7) to (43), (49), (54), (56), (5)
8), (60) to (64), (73) to (82), (8)
4) to (90), (92), (223) to (225),
(227) to (233), (235) to (240), and (242) to (244) each showed a mortality of 80% or more.

Test Example 3 [Heliothis vir
Insecticidal Test Against Escens] 0.2 ml of a dilution of water (100 ppm) of the test compound preparation obtained in Formulation Example 1 was dropped on the surface of a 3 g artificial feed prepared in a 30 ml polyethylene cup and spread uniformly. Was. After air drying, Heliothis vi
One second instar larva of rescens was released per cup. Ten animals were tested per treatment. After 7 days, the larval mortality was determined. As a result, the compounds of the present invention (3) to (2)
2), (27) to (32), (34) to (53), (6)
0) to (65), (68), (69), (72) to (8)
2), (84), (86)-(93), (224)-
(234), (243) and (244) each showed a mortality of 80% or more. Test Example 4 [Helicoverpa
Insecticidal test against Armigera) A cotton leaf piece (5 cm diameter) was added to a dilution (100 ppm) of water of the test compound preparation obtained in Preparation Example 1 with 10
After immersion for 2 seconds and air-drying, it was placed in a 5.5 cm diameter polyethylene cup. Among them, one third instar larva of Helicoverpa armigera
One per cup. Ten animals were tested per treatment. Five days later, the larval mortality was determined. As a result, the compounds of the present invention (1), (5), (10), (13), (1)
5), (25), (34), (40), (49), (5)
1), (64), (77), (79) and (80) each showed a mortality of 80% or more.

Test Example 5 [Codling Moss (Cydia)
Insecticidal Test Against Pomonella] 0.2 ml of a dilution of water (100 ppm) of the test compound preparation obtained in Preparation Example 1 was dropped on the surface of a 3 g artificial feed prepared in a 30 ml polyethylene cup and uniformly. Spread out. After air-drying, wax paper (approximately 2.5 cm
Corner). There were four per processing. After 7 days, the larval mortality was determined. As a result, the compound (1) of the present invention,
(11) to (13), (15), (16), (19),
(22), (28), (29), (31)-(37),
(39)-(41), (45), (46), (48)-
(53), (60) to (62), (74) to (81),
(87), (203), (225), (227) to (2)
30), (232), (233), (233), (23)
5), (236), (238) and (244) each showed a mortality of 80% or more. Test Example 6 [Tetranychus u
Acaricidal test against rticae) About 20 female spider mite female adults were released into the plastic cup planted seven days after sowing (Primary leaf stage), and left for 6 days. A 200-fold dilution of the test compound preparation with water (500 pp
m) 15 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 treatment. As a result, the compounds of the present invention (28), (40) and (4)
The effect of 9) was-or ±, while the effect of compound (A) was +.

Test Example 7 [Musca do
Insecticidal Test for Mesica)] 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 is added. 7
Then, about 30 mg of sucrose was uniformly added as a bait. Ten female female house flies were released into them, and after 1 day with the lid covered, their survival was examined to determine the mortality. As a result, the compounds of the present invention (9), (27), (29),
(31), (40), (52), (54), (20)
3), (223) to (225), (227) and (22)
9) showed a mortality of 80% or more. In contrast, the mortality of the compound (A) was 0%.

[0233]

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

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 251/54 C07C 251/54 251/60 251/60 255/62 255/62 309/65 309/65 309/73 309/73 309/75 309/75 323/12 323/12 323/20 323/20 323/47 323/47 333/04 333/04 333/08 333/08 C07D 213/30 C07D 213/30 213/61 213/61 213/64 213/64 241/12 241/12

Claims (36)

[Claims] 1. Equation (1) In the formula, R ¹ , R ² and R ³ each independently represent a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a nitro group or a cyano group. R ⁴ represents 3,
Represents 3-dihalogeno-2-propenyl group, a represents an integer of 0 to 2, Y represents an oxygen atom, a sulfur atom or an NH group, Z is an oxygen atom, a sulfur atom or NR ⁵ group, ^{R 5} Represents a hydrogen atom, an acetyl group or a C1-C3 alkyl group, and R ⁶ represents a hydrogen atom, a C1-C8 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl. Group, a C3-C6 haloalkynyl group, a triphenylmethyl group, a C3-C7 cycloalkyl group in which the ring is optionally substituted with a C1-C4 alkyl group, and a C3-C7 cycloalkyl group in which the ring is substituted with a C1-C4 alkyl group A good C4 to C10 (cycloalkylalkyl) group, a C5 to C6 cycloalkenyl group whose ring portion may be substituted with a C1 to C4 alkyl group or a C1 to C6 (cycloalkylalkyl) group Represents a C6-C8 (cycloalkenylalkyl) group which may be substituted by a 4-alkyl group, or represents a cyano group, a nitro group, a (C1-C4 alkoxy) carbonyl group, a C1-C4 alkylthio group or a C1-C4 alkoxy group Optionally substituted with a group
Represents a -C6 alkyl group or a compound of the formula (2) (In the formula, b represents an integer of 0 to 5, and (R ¹⁰ ) _b represents 0
From 5 identical or different halogen atoms, C1 to
C6 alkyl group, C1-C3 haloalkyl group, C2-C
6 alkenyl group, C2-C6 haloalkenyl group, C2-
C6 alkynyl group, C2-C6 haloalkynyl group, C1
-C6 alkoxy group, C1-C3 haloalkoxy group, C
3-C6 alkenyloxy group, C3-C6 haloalkenyloxy group, C3-C6 alkynyloxy group, C3-C
6 haloalkynyloxy group, (C1-C5 alkoxy)
Represents a carbonyl group, a cyano group or a nitro group,
R ¹¹ , R ¹² , R ¹³ and R ¹⁴ each independently represent a hydrogen atom, a C1-C3 alkyl group or a trifluoromethyl group, D represents a —CH ＝ group or a nitrogen atom, and J represents an oxygen atom or Represents a sulfur atom, 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 is a C1-C6 alkyl group, C1-C3
Haloalkyl group, C2-C6 alkenyl group or C3
Represents a phenyl group which may be substituted with a C1 to C6 cycloalkyl group, or a halogen atom, a C1 to C4 alkyl group, a C1 to C3 haloalkyl group, a C1 to C4 alkoxy group or a C1 to C3 haloalkoxy group;
R ¹⁶ and R ⁴² are each independently a C1-C6 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl group, a C3-C6 haloalkynyl group or C3
Represents a C6 cycloalkyl group, or a phenyl group which may be substituted with a halogen atom, a C1-C4 alkyl group, a C1-C3 haloalkyl group, a C1-C4 alkoxy group or a C1-C3 haloalkoxy group. Or a benzyl group in which the ring portion may be substituted with a halogen atom, a C1-C4 alkyl group, a C1-C3 haloalkyl group, a C1-C4 alkoxy group or a C1-C3 haloalkoxy group. ^T 1 -1, T represented by)
^{1 -2, T 1 -3, T} 1 -4, T 1 -5, represents ^T 1 -6 or ^T 1 -7, ^{R 7} is a hydrogen atom, C1 -C6 alkyl groups, C1 to C3 haloalkyl group or C3 ~ C6 cycloalkyl group or a halogen atom, C1
-C4 alkyl group, C1-C3 haloalkyl group, C1-
Represents a phenyl group which may be substituted with a C3 alkoxy group or a C1 to C3 haloalkoxy group, or
The ring is a halogen atom, a C1-C4 alkyl group, a C1-C4
3 haloalkyl group, C1-C3 alkoxy group or C
A represents a benzyl group which may be substituted with a 1 to C3 haloalkoxy group, and A represents a compound of the formula (3) A-1: -U ^1- (CR ¹⁹ R ²⁰ ) _t- (CR ²³ =
_{^{CR 24) h - (CR 25}} R 26) u - (CR 27 = C
_{^{R 28) p - (CR 29}} R 30) j - A-2: -U 2 - (CR 19 R 20) j - (CR 23 =
_{^{CR 24) h - (CR 25}} R 26) u - (CR 27 = C
_{^{R 28) p - (CR 29}} R 30) v - A-3: -U 1 - (CR 19 R 20) t - (CR 23 =
CR ²⁴ ) _h- (CR ²⁵ R ²⁶ ) _j -Q ^1- (CR
_{^{27 R 28) v - (CR}} 29 = CR 30) p - (CR
_{^{31 R 32) w - A-}} 4: -U 2 - (CR 19 R 20) j - (CR 23 =
CR ²⁴ ) _h- (CR ²⁵ R ²⁶ ) _v -Q ^1- (CR
_{^{27 R 28) w - (CR}} 29 = CR 30) p - (CR
_{^{31 R 32) x - A-}} 5: -U 1 - (CR 19 R 20) t -Q 1 - (CR
_{^{23 R 24) h -E- (CR}} 25 R 26) p - A-6: -U 1 - (CR 19 R 20) t -Q 1 - (CR
_{^{23 R 24) j -C≡C- (CR}} 25 R 26) m - [ ^{wherein, R 19, R 20, R} 23, R 24, R 25, R
²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ³¹ and R
³² independently represents a hydrogen atom, a C1 to C3 alkyl group or a trifluoromethyl group, h represents 0 or 1, j represents an integer of 1 to 3, and m represents an integer of 1 to 3 , P represents 0 or 1, t represents an integer of 0 to 3, u represents an integer of 0 to 3, v represents an integer of 1 to 4, w represents an integer of 1 to 4, x represents Represents an integer of 1 to 4, Q ¹ represents an oxygen atom, an S (O) _y group or an NR ³³ group, R ³³ represents a hydrogen atom or a C 1 to C 3 alkyl group, and y is an integer of 0 to 2. And E represents a C5-C6 cycloalkylene group. U ¹ is the formula ⁽⁴⁾ -G 1 -W- (wherein, W is represents a heterocyclic ring which may optionally be a benzene ring or substituted also be substituted, ^{G 1} has the formula ⁽⁵⁾ G 1 -1 _{^{:-( CR 35 R 36) a1 -}} G 1 -2 :-( CR 35 R 36) b1 -Q 2 - (CR
³⁷ R ³⁸ ) _d1 − (wherein Q ² represents an oxygen atom, an S (O) _z group or NR ³⁴
R ³⁴ represents a hydrogen atom or a C1-C3 alkyl group, and z represents an integer of 0-2. R ³⁵ , R ³⁶ ,
R ³⁷ and R ³⁸ each independently represent a hydrogen atom,
Represents a 1-C3 alkyl group or a trifluoromethyl group, (a1) represents an integer of 0-4, and (b1) represents 1-3
And (d1) represents an integer of 0 to 2. ) Represents a ^G 1 -1 or ^G 1 -2 represented by. Wherein U ² is a group represented by the formula (6) -G ¹ -W-G ^2- (wherein W and G ¹ have the same meanings as above, G ² is an oxygen atom, S (O) _e1 or NR ³⁹ ;
³⁹ represents a hydrogen atom or a C1-C3 alkyl group,
(E1) represents an integer of 0 to 2. ). A-1, A-2, A-3, A-4, A
Represents -5 or A-6. An oxime compound represented by｝. 2. In the above formulas (4) and (6), W is
A benzene ring, or a 6-membered heterocyclic ring containing at least one oxygen, sulfur, or nitrogen atom, or a 5-membered heterocyclic ring containing at least one oxygen, sulfur, or nitrogen atom Alternatively, when these rings are 1 to 4 identical or different R ⁴⁰ (where R ⁴⁰ is a halogen atom, a C1-C4 alkyl group,
Represents a 1 to 3 haloalkyl group, a 1 to 3 alkoxy group or a 1 to 3 haloalkoxy group. The oxime compound according to claim 1, which is a ring substituted with a). 3. In the above formulas (4) and (6), W is
A benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a furan ring, a thiophene ring, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a pyrazole ring or an imidazole ring, or The oxime compound according to claim 1 or 2, wherein the ring is a ring substituted with 1 to 4 identical or different R ^{40 s} (R ⁴⁰ has the same meaning as described above). 4. In the above formulas (4) and (6), W is
A benzene ring, a pyridine ring or a pyridazine ring, or a ring substituted with one to four identical or different R ^{40 s} (R ⁴⁰ has the same meaning as described above). Item 4. The oxime compound according to item 1, 2 or 3. 5. In the above formulas (4) and (6), W is a furan ring, a thiophene ring or a pyrrole ring, or these rings are one to three identical or different R ⁴⁰ (R The oxime-based compound according to claim 1, 2 or 3, wherein ⁴⁰ is a ring substituted with the above. 6. In the above formulas (4) and (6), W is a benzene ring, a 2,3-pyridinediyl group, a 2,4-pyridinediyl group, a 2,5-pyridinediyl group, a 2,6-pyridine Diyl group, 3,5-pyridinediyl group, 3,4-pyridinediyl group, 3,4-pyridazinediyl group, 3,5
A -pyridazinediyl group or a 3,6-pyridazinediyl group, or these rings are substituted with 1 to 4 identical or different R ^{40 s} (R ⁴⁰ has the same meaning as described above). 5. A ring according to claim 1, 2, 3 or 4.
2. The oxime compound according to item 1. 7. In the above formula (1), R ⁶ is a hydrogen atom,
C1-C8 alkyl group, C2-C6 haloalkyl group, C
3-C6 alkenyl group, C3-C6 haloalkenyl group,
A C3-C6 alkynyl group, a C3-C6 haloalkynyl group, a triphenylmethyl group, a C3-C7 cycloalkyl group whose ring portion may be substituted with a C1-C4 alkyl group, and a ring portion substituted with a C1-C4 alkyl group C4 to C10 (cycloalkylalkyl) group which may be substituted, C5 to C10 wherein the ring portion may be substituted by a C1 to C4 alkyl group
6 cycloalkenyl or group or ring portion is a C1~C4 alkyl group optionally substituted C6-C8 (cycloalkenyl alkyl) group, or, ^T 1 -1 or ^T 1 -2 in the formula (2) ^(T 1 -1 and ^T 1 -2 are as defined above.) oxime compound according to claim 1 is. 8. The oxime compound according to claim 1, wherein both Y and Z in the formula (1) are oxygen atoms. 9. The oxime compound according to claim 1, wherein a is 0 in the formula (1). 10. In the above formula (1), R ¹ , R ² and R ³ each independently represent a halogen atom or C1 to C
The oxime compound according to any one of claims 1 to 9, which is a trialkyl group. 11. In the formula (1), A is A-1, A
-2, A-3 or A-4 (A-1, A-2, A-3 and A-4 represent the same meaning as described above).
10. The oxime compound according to any one of 10. 12. In the formula (1), A is A-1 (A
-1 represents the same meaning as described above. ).
The oxime compound according to any one of the above. 13. In the formula (1), A is A-2 (A
-2 represents the same meaning as described above. ).
The oxime compound according to any one of the above. 14. The oxime compound according to claim 13, wherein in the formula (6), G ² is an oxygen atom. 15. In the above formulas (4) and (6), G ¹
There ^G 1 -1 ^(G 1 -1 represents. As defined above) oxime compound according to any one of claims 1 to 14 is. 16. In the above formulas (4) and (6), G ¹
There ^G 1 -2 ^(G 1 -2 represents. As defined above) oxime compound according to any one of claims 1 to 14 is. 17. The oxime compound according to claim 16, wherein Q ² is an oxygen atom. 18. In the above formula (1), R ⁶ is a hydrogen atom, C1-C8 alkyl group, C2-C6 haloalkyl group, C3-C6 alkenyl group, C3-C6 haloalkenyl group, C3-C6 alkynyl group or C3 -C6 haloalkynyl group, a C3-C7 cycloalkyl group whose ring portion may be substituted with a C1-C4 alkyl group,
C4 to C10 which may be substituted with a C4 alkyl group
A (cycloalkylalkyl) group, a C5-C6 cycloalkenyl group in which the ring portion may be substituted with a C1-C4 alkyl group or a C6-C8 (cycloalkenyl) in which the ring portion may be substituted with a C1-C4 alkyl group. The oxime compound according to any one of claims 1 to 17, which is an (alkyl) group. 19. In the above formula (1), R ⁶ is T ¹ -1.
Alternatively ^T 1 -2 ^(T 1 -1 and ^T 1 -2 are as defined above.) Oxime compound according to any one of claims 1 to 17 is. 20. The oxime compound according to claim 1, wherein in the formula (1), R ⁶ is a hydrogen atom. 21. In the above formula (1), R ⁶ is C1 to C
8 alkyl groups, C2-C6 haloalkyl groups, C3-C6
The oxime compound according to any one of claims 1 to 18, which is an alkenyl group or a C3-C6 haloalkenyl group. 22. In the above formula (1), R ² and R ³ are each independently a halogen atom or a C1-C3 alkyl group, R ⁴ is a 3,3-dichloro-2-propenyl group, and a Is 0, Y and Z are both oxygen atoms, R ⁶ is a C1-C8 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group or a C3-C6 haloalkenyl group, and A is A-1 (A-1 represents the same meaning as described above), h and p are both 0, and R
^{19, R 20, R 25,} R 26, R 29 and ^{R 30} are both hydrogen atoms, ^{G 1} in formula (4) ^{G 1} -
It is 1 ^(G 1 -1 are as defined above.), (A
1) is 0 and W is a 1,3-phenylene group or 1,
The oxime compound according to claim 1, which is a 4-phenylene group. 23. In the above formula (1), R ² and R ³ are each independently a halogen atom or a C1-C3 alkyl group, R ⁴ is a 3,3-dichloro-2-propenyl group, a is 0, Y and Z are both oxygen atoms, R ⁶ is a C1-C8 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group or a C3-C6 haloalkenyl group, and A is A- 2 (A-2 represents the same meaning as described above), h and p are both 0, and R
^{19, R 20, R 25,} R 26, R 29 and ^{R 30} are both hydrogen atoms, ^{G 1} in formula (6) is ^{G 1} -
It is 1 ^(G 1 -1 are as defined above.), (A
1) is 0, G ² is an oxygen atom, and W is 1,3-
The oxime compound according to claim 1, which is a phenylene group or a 1,4-phenylene group. 24. An insecticide or acaricide comprising the oxime compound according to any one of claims 1 to 23 as an active ingredient. 25. Equation (7) In the formula, R ² , R ³ , R ⁷ , R ¹⁹ , R ²⁰ and j represent the same meaning as described above, and R ⁴¹ represents 3,3-dichloro-2-
Represents a propenyl group, a 3,3-dibromo-2-propenyl group or a 3-bromo-3-chloro-2-propenyl group. Compound represented by｝. 26. In the above formula (7), R ² and R
³ are each independently a halogen atom or C1 to C3
R ⁷ is a hydrogen atom, a C1-C6 alkyl group or a C1-C3 haloalkyl group, or a halogen atom, a C1-C4 alkyl group, a C1-C3
Haloalkyl group, C1-C3 alkoxy group or C1
~C3 be substituted with a haloalkoxy group is also a phenyl group, A compound according to claim 25 R ¹⁹ and R ²⁰ are both hydrogen atoms. 27. Equation (8) 中 wherein R ² , R ³ , R ⁷ , R ¹⁹ , R ²⁰ , R ²⁹ ,
R ³⁰ , R ⁴¹ , v and j represent the same meaning as described above. ｝
A compound represented by the formula: 28. In the formula (8), R ² and R
³ are each independently a halogen atom or C1 to C3
R ⁷ is a hydrogen atom, a C1-C6 alkyl group or a C1-C3 haloalkyl group, or a halogen atom, a C1-C4 alkyl group, a C1-C3
Haloalkyl group, C1-C3 alkoxy group or C1
A phenyl group which may be substituted with ~C3 haloalkoxy ^group, R ^19, R ^20, compound of claim 27, wherein ^{R 29} and ^{R 30} are all hydrogen atoms. 29. Equation (9) Wherein R ¹ , R ² , R ³ , R ⁶ , R ⁷ , A, Z and a
Has the same meaning as described above. A phenolic compound represented by｝ (excluding compounds in which R ⁶ is a hydrogen atom). 30. The phenolic compound according to claim 29, wherein in the formula (9), Z is an oxygen atom. 31. The phenolic compound according to claim 29, wherein a is 0 in the formula (9). 32. In the above formula (9), R ¹ , R ² and R ³ each independently represent a halogen atom or C1 to C2.
The phenolic compound according to any one of claims 29 to 31, which is an alkyl group of (3). 33. In the formula (9), A is A-1 (A
-1 represents the same meaning as described above. ).
2. The phenolic compound according to any one of 2. 34. In the formula (9), A is A-2 (A
-2 represents the same meaning as described above. ).
2. The phenolic compound according to any one of 1. 35. In the formula (9), R ² and R ³ are each independently a halogen atom or a C1 to C3 alkyl group, a is 0, Z is an oxygen atom,
⁶ is a C1-C8 alkyl group, a C2-C6 haloalkyl group, a C3-C6 alkenyl group or a C3-C6 haloalkenyl group, and A is A-1 (A-1 has the same meaning as described above). ), H and p are both 0, and R
¹⁹ , R ²⁰ , R ²⁵ , R ²⁶ , R ²⁹ and R ³⁰ are all hydrogen atoms, and G ¹ in the formula (4) is G ¹ −
It is 1 ^(G 1 -1 are as defined above.), (A
1) is 0 and W is a 1,3-phenylene group or 1,
The phenolic compound according to claim 29, which is a 4-phenylene group. 36. In the above formula (9), R ² and R ³ are each independently a halogen atom or a C1 to C3 alkyl group, a is 0, Z is an oxygen atom,
⁶ is a C1-C8 alkyl group, C2-C6 haloalkyl group, C3-C6 alkenyl group or C3-C6 haloalkenyl group, and A is A-2 (A-2 has the same meaning as described above). ), H and p are both 0, and R
^{19, R 20, R 25,} R 26, R 29 and ^{R 30} are both hydrogen atoms, ^{G 1} in formula (6) is ^{G 1} -
It is 1 ^(G 1 -1 are as defined above.), (A
1) is 0, G ² is an oxygen atom, and W is 1,3-
30. The phenolic compound according to claim 29, which is a phenylene group or a 1,4-phenylene group.