JP2003040864A - Phthalic acid diamide compound and pest-controlling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new agrochemical, especially an insecticidal and acaricidal agent. SOLUTION: The phthalic acid diamide compound represented by general formula (1) [wherein, V<1> to V<4> are each a carbon atom or a nitrogen atom; W<1> and W<2> are each independently an oxygen atom or a sulfur atom; X<1> is pyrrole, tetrazole or the like; X<2> is a hydrogen atom, a halogen atom, a 1-6C alkyl or the like; Y is a halogen atom, a 1-6C alkyl, a 1-6C haloalkyl, a 1-6C haloalkoxy, a 1-6C haloalkoxy-1-6C haloalkoxy or the like; R<1> is a 1-6C alkyl, a 1-6C alkylthio-1-6C alkyl, a 1-6C alkylsulfinyl-1-6C alkyl, a 1-6C alkylsulfonyl-1-6C alkyl, a 1-6C alkoxyimino-1-6C alkyl or the like; R<2> and R<3> are each independently a hydrogen atom, a 1-6C alkyl or the like; m is an integer of 1-3; and n is an integer of 1-5], the salt thereof, and the pest- controlling agent containing the compound are provided.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel phthalic acid diamide compound and a salt thereof, and a pest control agent containing the compound as an active ingredient. The pest control agent in the present invention means a pest control agent for harmful arthropods in the fields of agriculture and horticulture, livestock, and hygiene (animal drugs, domestic and commercial insecticides). Further, the pesticide in the present invention means an insecticidal / miticide, a nematicide, a herbicide and a fungicide in the field of agriculture and horticulture.

[0002]

2. Description of the Related Art Conventionally, regarding phthalic acid diamide derivatives similar to the present invention, European Patent Application Publication (EP 0,9
19,542, EP 1,006,107,), International Patent Application (WO 01/00575, WO 01/00599, WO 01 /
No. 02354, WO 01/21576) are disclosed to have insecticidal activity. However, nothing is disclosed regarding the novel phthalic acid diamide compound according to the present invention.

[0003]

Problems to be Solved by the Invention Due to the long-term use of pesticides such as insecticides and fungicides, pests have acquired resistance in recent years, and it is difficult to control them by the conventionally used insecticides and fungicides. It has become. Moreover, some of the existing pest control agents are highly toxic, or some of them are disturbing the ecosystem due to long-term persistence. Under such circumstances, the development of new pest control agents with low toxicity and low residue is always expected.

[0004]

As a result of intensive studies aimed at solving the above problems, the present inventors found that the novel phthalic acid diamide compound represented by the general formula (1) according to the present invention is excellent. Pest control activity, especially insecticidal and acaricidal activity,
Moreover, they have found that they are extremely useful compounds with almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects, and completed the present invention.

That is, the present invention relates to the following [1] to [4].

[1] General formula (1):

[0007]

[Chemical 6]

[In the formula, V ¹ , V ² , V ³ and V ⁴ each independently represent a carbon atom or a nitrogen atom, and W ¹ and W ² each independently represent an oxygen atom or a sulfur atom. , X ¹ is the expression from X ¹ -1
Represents a heterocycle represented by any of X ¹ -11,

[0009]

[Chemical 7]

X²Is a hydrogen atom, halogen atom, C₁~ C₆A
Rukiru, C₁~ C₆Haloalkyl, C₁~ C₆Alkoxy, C₁~
C₆Haloalkoxy, C₁~ C₆Alkylthio or C₁~ C₆Halo
When alkylthio is represented and m is an integer of 2 or more,
Each X²Are the same or different
Also, Y is hydrogen atom, halogen atom, cyano, -SC
N, -SF_Five, Nitro, azide, C₁~ C ₆Alkyl, R^FiveBy
Arbitrarily replaced by (C₁~ C₆) Alkyl, C₃~ C₈Cycloa
Rukiru, C₃~ C₈Halocycloalkyl, C₂~ C₆Archeni
Le, R^FiveArbitrarily replaced by (C₂~ C₆) Alkenyl,
C₂~ C₆Alkynyl, R^FiveArbitrarily replaced by (C₂~ C
₆) Alkynyl, -OH, -OR⁶, -OCHO, -SH, -SR⁶, -S (O)
R⁶, -S (O)₂R⁶, -NHR⁷, -N (R⁷) R⁶, -N (R⁷) CHO, -CHO, -C
(O) R⁸, -C (O) OR⁸, -C (O) SR⁸, -C (S) OR⁸, -C (S) SR⁸, -C
(O) NHR⁹, -C (O) N (R⁹) R⁸, -CH = NOR^Ten, -C (= NOR^Ten) R⁸, -C
(= NOR^Ten) OR⁸, -C (= NOR^Ten) SR⁸, -C (= NOR^Ten) NH (R⁹), -C (=
NOR^Ten) N (R⁹) R⁸, -P (O) (OR¹¹)₂, -P (S) (OR^{1 1})₂, -P (O) (R
¹⁴) (OR¹¹), -SiR¹²R¹³R¹⁴, (Z)_pHas been replaced by
May be phenyl, (Z)_qMay be replaced by
Naphthyl, L or M, and n is an integer of 2 or more
Each Y is the same or different
And n is 2 and two Ys are adjacent to each other.
Two adjacent Y's are -CH₂CH ₂CH₂-, -CH₂CH
₂O-, -CH₂OCH₂-, -OCH₂O-, -CH₂CH₂S-, -CH₂SCH₂-, -CH
₂CH₂N (R^Four)-, -CH₂N (R^Four) CH₂-, -CH₂CH = CH-, -OCH = CH-,-
SCH = CH-, -N (R^Four) CH = CH-, -OCH = N-, -SCH = N-, -N (R^Four) CH = N
-, -N (R^Four) N = CH-, -CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂O-, -CH₂
OCH₂CH₂-, -OCH₂CH₂O-, -CH₂OCH₂O-, -CH = CHCH = CH-, -N
= CHCH = CH- or -N = CHN = CH- forming Y
May form a 5- or 6-membered ring with the atom
, The hydrogen atom bonded to each carbon atom is R¹⁵By
Optionally substituted, L is represented by the formula L-1 to the formula L-58.
Represents an aromatic heterocycle represented by any of

[0011]

[Chemical 8]

[0012]

[Chemical 9]

M represents an aliphatic heterocycle represented by any of the formulas M-1 to M-28,

[0014]

[Chemical 10]

R¹, R²And R³Are each independently a hydrogen atom,
Cyano, C₁~ C₁₂Alkyl, R¹⁶Arbitrarily replaced by
(C₁~ C₁₂) Alkyl, C₃~ C₈Cycloalkyl, C₃~ C₈
Halocycloalkyl, C₃~ C₁₂Alkenyl, R¹⁶By
Arbitrarily substituted (C₃~ C₁₂) Alkenyl, C₃~ C₈Cyclo
Alkenyl, C₃~ C₈Halocycloalkenyl, C₃~ C₁₂A
Lucinyl, R¹⁶Arbitrarily replaced by (C₃~ C₈) Al
Quinyl, -OR¹⁷, -N (R¹⁸) R¹⁷, -SR¹⁹, -S (O)₂R¹⁹, -SN (R
^{twenty one}) R²⁰, -SN (R^{twenty three}) C (O) OR^{twenty two}, -S (O)₂N (R^{twenty five}) R^{twenty four}, -C (O)
R⁸, -C (O) OR⁸, -C (O) SR⁸, -C (S) R⁸, -C (S) OR⁸, -C (S) SR
⁸, -C (O) N (R^{twenty five}) R^{twenty four}Or R¹And R²Together with
Becomes C₂~ C₆By forming an alkylene chain,
It may form a 3- to 7-membered ring together with the nitrogen atom to be bonded,
When this alkylene chain is oxygen atom, sulfur atom or nitrogen
It may contain 0 to 2 atoms, and is a halogen atom or a
Optionally substituted by chill, R^FourIs a hydrogen atom,
C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₆Archeni
Le, C₃~ C₆Haloalkenyl, C₃~ C₆Alkynyl, C₃~ C₆
Haloalkynyl, C₁~ C₆Alkoxycarbonyl (C₁~ C_Four)
Alkyl, C₁~ C₆Haloalkoxycarbonyl (C₁~ C_Four)
Rukiru, C₁~ C₆Alkoxy, C₁~ C₆Alkoxy Carboni
Le, C₁~ C₆Haloalkoxycarbonyl, (Z)_pSet by
Optionally substituted phenyl or (Z)_pReplaced by
Optionally substituted by phenyl (C₁~ C_Four) Al
Represents a kill, R^FiveIs a halogen atom, C₃~ C₈Cycloalk
Le, C₃~ C₈Halocycloalkyl, -OH, -OR²⁶, -SH, -SR
²⁶, -S (O) R²⁶, -S (O)₂R²⁶, -NHR²⁷, -N (R²⁷) R²⁶, C₁~ C
₆Alkoxycarbonyl, C₁~ C₆Haloalkoxy carbo
Nil, -SiR¹²R¹³R¹⁴, (Z)_pMay be replaced by
Phenyl, (Z)_qNaphthi optionally substituted by
R, L or M, R⁶Is C₁~ C₆Alkyl, R²⁸By
Arbitrarily replaced by (C₁~ C₆) Alkyl, C₃~ C₈Cycloa
Rukiru, C₃~ C₈Halocycloalkyl, C₂~ C₆Archeni
Le, R²⁸Arbitrarily replaced by (C₂~ C₆) Archeni
Le, C₃~ C₈Cycloalkenyl, C₃~ C₈Halo cyclo arce
Nil, C₃~ C₆Alkynyl, R²⁸Arbitrarily replaced by
(C₃~ C₆) Alkynyl, -C (O) R⁸, -C (O) OR⁸, -C (O) N
(R⁹) R⁸, -S (O)₂R⁸, -S (O)₂N (R⁹) R⁸, -P (O) (OR¹¹)₂, -P
(S) (OR¹¹)₂, (Z)_pPheny optionally substituted by
Le, (Z) _qNaphthyl optionally substituted by L, L or
Represents M, R⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆
Haloalkyl, C₃~ C₆Alkenyl, C₃~ C₆Halo archeni
Le, C₃~ C₆Alkynyl, C₃~ C₆Haloalkynyl, -CHO,
C₁~ C₆Alkylcarbonyl, C₁~ C₆Haloalkyl carbo
Nil, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Halo arco
Xycarbonyl, C₁~ C₆Alkylsulfonyl, C₁~ C₆Ha
Roalkylsulfonyl, (Z)_pEven if replaced by
Good phenylcarbonyl or (Z)_pHas been replaced by
Optionally substituted by phenyl (C₁~ C_Four) Arkoki
Represents carbonyl or R⁶And R⁷Together with
C₂~ C_FiveBond by forming an alkylene chain
A 3- to 6-membered ring may be formed with the nitrogen atom at this time.
This alkylene chain contains 0 to 2 oxygen atoms or sulfur atoms.
And may be replaced by a halogen atom or methyl
R may be⁸Is C₁~ C₆Alkyl, C₁~ C₆Halo
Alkyl, C₃~ C₈Cycloalkyl, C₃~ C₈Halo cycloa
Rukiru, C₃~ C₈Cycloalkyl (C₁~ C_Four) Alkyl, C₁~
C₆Alkoxy (C₁~ C_Four) Alkyl, C₁~ C₆Alkylthio (C
₁~ C_Four) Alkyl, C₂~ C₆Cyanoalkyl, C₂~ C₆Arche
Nil, C₂~ C₆Haloalkenyl, C₂~ C₆Alkynyl, C₃~
C₆Haloalkynyl, (Z)_pMay be replaced by
Phenyl, (Z)_pPhenyl optionally substituted by
Replaced by (C₁~ C_Four) Alkyl, (Z)_qSet by
Optionally substituted naphthyl, represents L or M, R⁹Is water
Elementary atom, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₆
Alkenyl or C₃~ C₆Represents alkynyl or R⁸
And R⁹Together with C₂~ C_FiveCan form an alkylene chain
Form a 3- to 6-membered ring with the nitrogen atom to which
At this time, the alkylene chain may be an oxygen atom or a sulfur atom.
It may contain 0 to 2 yellow atoms, and a halogen atom or
Optionally substituted by methyl, R^TenIs the hydrogen source
Child, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈Shiku
Lower alkyl, C₃~ C₆Alkenyl, C₃~ C₆Halo archeni
Le, C₃~ C₆Alkynyl, C₃~ C₆Haloalkynyl or (Z)_p
Substituted by phenyl, which may be substituted by
(C₁~ C_Four) Represents alkyl, R¹¹Is C₁~ C₆Alkyl
Or C₁~ C₆Represents haloalkyl, R¹²And R¹³Are each German
Stand up C₁~ C₆Represents alkyl, R¹⁴Is C₁~ C₆Alkyl
Or (Z)_pTable showing phenyl optionally substituted by
Then R¹⁵Is a halogen atom, cyano, nitro, C₁~ C₆A
Rukiru, C₁~ C₆Haloalkyl, C₂~ C₆Alkenyl, C₂~
C₆Haloalkenyl, C₂~ C₆Alkynyl, C₂~ C₆Halo al
Quinyl, C₁~ C₆Alkoxy, C₁~ C₆Haloalkoxy, C₁
~ C₆Alkylthio, C₁~ C₆Haloalkylthio, C₁~ C₆A
Ruquilsulfinyl, C₁~ C₆Haloalkylsulfini
Le, C₁~ C₆Alkylsulfonyl, C₁~ C₆Haloalkyls
Lefonil, C₁~ C₆Alkylamino, di (C₁~ C₆) Alkyl
Amino, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Halo al
Coxycarbonyl, (Z)_pMay be replaced by
Phenyl, (Z)_qNaphthi optionally substituted by
Represents L, L or M, and more than one R at the same time¹⁵Replace with
If each R¹⁵Are the same as each other,
Or they may be different, R¹⁶Is a halogen atom,
Cyano, nitro, C₃~ C₈Cycloalkyl, C₃~ C₈Haroshi
Chroalkyl, -CHO, -C (O) R⁸, -C (O) OR⁸, -C (O) SR⁸,-
C (O) N (R⁹) R⁸, -C (O) C (O) OR⁸, -CH = NOR^Ten, -C (= NOR^Ten)
R⁸, -OR²⁹, -N (R³⁰) R²⁹, -SH, -SR³¹, -S (O) R³¹, -S (O)
₂R³¹, -P (O) (OR¹¹)₂, -P (S) (OR¹¹)₂, -P (phenyl)₂, -P (O)
(Phenyl)₂, (Z)_pPheny optionally substituted by
Le, (Z)_qNaphthyl optionally substituted by L, L or
Represents M, R¹⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆
Haloalkyl, C₃~ C₆Alkenyl, C₃~ C₆Halo archeni
Le, C₃~ C₆Alkynyl, (Z)_pEven if replaced by
Good phenyl or (Z)_pMay be replaced by
Replaced by phenyl (C₁~ C_Four) Represents alkyl, R
¹⁸Is C₁~ C₆Alkylcarbonyl, C₁~ C₆Haloalkyl
Carbonyl, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Halo
Alkoxycarbonyl or (Z)_pHas been replaced by
Represents good phenylcarbonyl, R¹⁹Is C₁~ C₆Al
Kill, C₁~ C₆Haloalkyl, C₃~ C₆Alkenyl, C₃~ C₆
Haloalkenyl, C₃~ C₆Alkynyl, (Z)_pReplaced by
Optionally phenyl, (Z)_qHas been replaced by
May represent naphthyl, L or M, R²⁰And R^{twenty one}Are each
Independently C₁~ C₁₂Alkyl, C₁~ C₁₂Haloalkyl, C₂~
C_{1 2}Cyanoalkyl, C₁~ C₁₂Alkoxy (C₁~ C₁₂) Al
Kill, C₁~ C₁₂Alkoxycarbonyl (C₁~ C₁₂) Archi
Le, C₃~ C₁₂Alkenyl, C₃~ C₁₂Haloalkenyl, C₃~
C₁₂Alkynyl, C₃~ C₁₂Haloalkynyl, C₁~ C₆Archi
Lecarbonyl, (Z)_pMay be replaced by
Substituted by nil (C₁~ C_Four) Alkyl or (Z)_pBy
Represents an optionally substituted phenyl, or
R²⁰And R^{twenty one}Together with C_Four~ C₇Form an alkylene chain
Form a 5- to 8-membered ring with the nitrogen atom to which it is attached.
The alkylene chain may be an oxygen atom or
May contain 0 to 2 sulfur atoms, and C₁~ C_FourArchi
R may be substituted by R,^{twenty two}Is C₁~ C₁₂Al
Represents a kill, R^{twenty three}Is C₁~ C₆Alkyl or (Z)_pBy
Substituted by optionally substituted phenyl (C₁
~ C_Four) Represents alkyl, R^{twenty four}Is a hydrogen atom, C₁~ C₆Archi
Le, C₁~ C₆Haloalkyl, C₂~ C₆Alkenyl, C₂~ C₆A
Lucinyl, C₃~ C₈Cycloalkyl, C₂~ C₆Cyanoarch
Le, C₁~ C₆Alkoxy (C₁~ C_Four) Alkyl, C₁~ C₆Archi
Lecarbonyl, C₁~ C₆Alkoxy, C₁~ C₆Halo arcoki
Shi, (Z)_pBenzyloxy optionally substituted by
Shi, (Z)_pPhenyl optionally substituted by or
(Z)_pRepresents benzyl optionally substituted by R
^{twenty five}Is a hydrogen atom, C₁~ C₆Alkyl or C₁~ C₆Halo Archi
Or R^{twenty four}And R^{twenty five}Together with C_Four~ C₇
A nitrogen atom that binds by forming an alkylene chain
A 5- to 8-membered ring may be formed together with this
The xylene chain may contain 0 to 2 oxygen atoms or sulfur atoms.
And C₁~ C_FourMay be substituted by alkyl
R²⁶Is C₁~ C₆Alkyl, R³²Arbitrarily replaced by
(C₁~ C₆) Alkyl, C₃~ C₈Cycloalkyl, C₃~ C₈
Halocycloalkyl, C₂~ C₆Alkenyl, R³²By
Arbitrarily substituted (C₂~ C₆) Alkenyl, C₃~ C₆Alkini
Le, R³²Arbitrarily replaced by (C₃~ C₆) Arkini
Le, -C (O) R⁸, -S (O)₂R⁸, (Z)_pHas been replaced by
Good phenyl, (Z)_qMay be replaced by
Represents futyl, L or M, R²⁷Is a hydrogen atom, C₁~ C₆Al
Kill, C₁~ C₆Haloalkyl, C₃~ C₈Cycloalkyl, C₂
~ C₆Alkenyl, C₃~ C₆Alkynyl, (Z)_pReplaced by
Optionally phenyl, (Z)_qHas been replaced by
Optionally represents naphthyl, L or M, or R²⁶And R²⁷
Together with C₂~ C_FiveTo form an alkylene chain
Therefore, even if a 3- to 6-membered ring is formed with the nitrogen atom to be bonded,
Well, at this time, this alkylene chain is an oxygen atom or a sulfur source.
May contain 0 to 2 children, and halogen atom or methyl
R may be substituted by R,²⁸Is a halogen source
Child, cyano, C₃~ C₈Cycloalkyl, C₃~ C₈Halocyclo
Alkyl, -OH, -OR³³, -SH, -SR³³, -S (O) R³³, -S (O)₂
R³³, -NHR³⁴, -N (R³⁴) R³³, -C (O) R³³, -CHO, -C (O) OH,
-C (O) OR³³Or (Z)_pMay be replaced by
Represents nil, R²⁹Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C
₆Haloalkyl, C₃~ C₈Cycloalkyl, C₃~ C₈Haroshi
Croalkyl, C₁~ C₆Alkoxy (C₁~ C₆) Alkyl, C₁
~ C₆Alkylthio (C₁~ C₆) Alkyl, C₃~ C₆Archeni
Le, C₃~ C₆Haloalkenyl, C₃~ C₆Alkynyl, C₃~ C₆
Haloalkynyl, -CHO, C₁~ C₆Alkylcarbonyl, C₁
~ C₆Haloalkylcarbonyl, C₁~ C₆Alkoxy carbo
Nil, C₁~ C₆Haloalkoxycarbonyl, C₁~ C₆Archi
Luaminocarbonyl, di (C₁~ C₆) Alkylaminocarbo
Nil, C₁~ C₆Alkylaminothiocarbonyl, di (C₁~ C
₆) Alkylaminothiocarbonyl, -P (O) (OR¹¹)₂, -P
(S) (OR¹¹)₂, (Z)_pPheny optionally substituted by
Le, (Z)_pBy phenyl optionally substituted by
Replaced by (C₁~ C_Four) Alkyl, (Z)_qReplaced by
Optionally represents naphthyl, represents L or M, R³⁰Is the hydrogen source
Child, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C₆Al
Kircarbonyl, C₁~ C₆Haloalkylcarbonyl, C₁~
C₆Alkoxycarbonyl, C₁~ C₆Haloalkoxy carbo
Nil, C₁~ C₆Alkylsulfonyl, C₁~ C₆Haloalkyl
Sulfonyl, (Z)_pPheny optionally substituted by
Lecarbonyl or (Z)_pMay be replaced by
Replaced by phenyl (C₁~ C_Four) Alkoxycarboni
Or R²⁹And R³⁰Together with C₂~ C_Five
A nitrogen atom that binds by forming an alkylene chain
May form a 3- to 6-membered ring together with the
The xylene chain may contain 0 to 2 oxygen atoms or sulfur atoms.
And substituted by halogen atom or methyl
May be R³¹Is C₁~ C₈Alkyl, R³⁵By any
Replaced (C₁~ C₈) Alkyl, C₃~ C₈Cycloalkyl,
C₃~ C₈Halocycloalkyl, C₃~ C₆Alkenyl, R³⁵To
Therefore, it is arbitrarily replaced (C₃~ C₆) Alkenyl, C₃~ C₆A
Lucinyl, R³⁵Arbitrarily replaced by (C₃~ C₆) Al
Quinyl, -CHO, -C (O) R³⁶, -C (S) R³⁶, -C (= NR³⁷) R³⁶, -S
H, C₁~ C₆Alkylthio, C₁~ C₆Haloalkylthio, -P
(O) (OR¹¹)₂, -P (S) (OR¹¹)₂, (Z)_pHas been replaced by
May be phenyl, (Z)_pMay be replaced by
Phenylthio, (Z)_qNaphth that may be replaced by
Represents chill, L or M, R³²Is a halogen atom, cyano, C
₃~ C₈Cycloalkyl, C₃~ C₈Halocycloalkyl, C₁
~ C₆Alkoxy, C₁~ C₆Haloalkoxy, C₁~ C₆Archi
Lucio, C₁~ C₆Haloalkylthio, C₁~ C₆Alkylsul
Finil, C₁~ C₆Haloalkylsulfinyl, C₁~ C₆A
Lucylsulfonyl, C₁~ C₆Haloalkylsulfonyl, C₁
~ C₆Alkylcarbonyl, C₁~ C₆Haloalkylcarboni
Le, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Halo arcoki
Sicarbonyl, (Z)_pMay be replaced by
Nil, (Z)_pA phenoxy, optionally substituted by
(Z)_pPhenylthio optionally substituted by (Z)_q
Represents naphthyl, L or M optionally substituted by
Then R³³Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃
~ C₈Cycloalkyl, C₃~ C ₈Halocycloalkyl, C₃~
C₆Alkenyl, C₃~ C₆Haloalkenyl, C₃~ C₈Cycloa
Lucenil, C₃~ C₈Halocycloalkenyl, C₃~ C₆Archi
Nil, C₃~ C₆Haloalkynyl, (Z)_pReplaced by
You can have phenyl, (Z)_qMay be replaced by
Represents naphthyl, L or M, R³⁴Is a hydrogen atom, C₁~ C₆
Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈Cycloalk
Le, C₃~ C₆Alkenyl, C₃~ C₆Alkynyl, (Z)_pBy
Optionally substituted phenyl, (Z)_qReplaced by
Optionally represents naphthyl, L or M, or R
³³And R³⁴Together with C₂~ C_FiveForm an alkylene chain
Form a 3- to 6-membered ring together with the nitrogen atom to which it is attached.
The alkylene chain may be an oxygen atom or
May contain 0 to 2 sulfur atoms, and is a halogen atom.
Or optionally substituted by methyl, R³⁵Is ha
Rogen atom, cyano, nitro, C₃~ C₈Cycloalkyl,
C₃~ C₈Halocycloalkyl, -CHO, -C (O) R⁸, -C (O) O
R⁸, -C (O) SR⁸, -C (O) N (R⁹) R⁸, -C (O) C (O) OR⁸, -CH = NOR
^Ten, -C (= NOR^Ten) R⁸, -OR²⁹, -N (R³⁰) R²⁹, -SH, -SR³⁸,-
S (O) R³⁸, -S (O)₂R³⁸, -P (O) (OR¹¹)₂, -P (S) (OR¹¹)₂, -P
(Phenyl)₂, -P (O) (phenyl)₂, (Z)_pHas been replaced by
Good phenyl, (Z)_qMay be replaced by
Represents futyl, L or M, R³⁶Is C₁~ C₆Alkyl, C₁~ C
₆Haloalkyl, C₃~ C₈Cycloalkyl, C₃~ C ₈Haroshi
Croalkyl, -OR³⁹, -SR³⁹, -NHR⁴⁰, -N (R⁴⁰) R³⁹,
(Z)_pPhenyl optionally substituted by (Z)_qBy
Represents optionally substituted naphthyl, L or M, R
³⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Alkoxy,
C₁~ C₆Alkylamino, di (C₁~ C₆) Alkylamino, C₁
~ C₆Alkoxycarbonyl, C₁~ C₆Haloalkoxycal
Bonil or (Z)_pPhenyl optionally substituted by
Represents R³⁸Is C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₈Cycloalkyl, C₃~ C ₈Halo cycloalk
Le, C₃~ C₆Alkenyl, C₃~ C₆Haloalkenyl, C₃~ C₆
Alkynyl, C₃~ C₆Haloalkynyl, C₁~ C₆Alkyr
Lebonil, C₁~ C₆Haloalkylcarbonyl, C₁~ C₆Al
Coxycarbonyl, C₁~ C₆Haloalkoxycarbonyl,
C₁~ C₆Alkylaminocarbonyl, di (C₁~ C₆) Alkyl
Aminocarbonyl, (Z)_pMay be replaced by
Phenyl, (Z)_pPhenyl optionally substituted by
Replaced by (C₁~ C_Four) Represents alkyl, L or M,
R³⁹Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈
Cycloalkyl, C₃~ C ₈Halocycloalkyl, C₃~ C₆A
Lucenil, C₃~ C₆Haloalkenyl, C₃~ C₆Alkynyl,
C₃~ C₆Haloalkynyl, (Z)_pEven if replaced by
Good phenyl, (Z)_pMay be replaced by
Substituted by nil (C₁~ C_Four) Represents alkyl, L or M
Then R⁴⁰Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Haloa
Rukiru, C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo Archi
Lecarbonyl, C₁~ C₆Alkoxycarbonyl or C₁~ C₆
Represents haloalkoxycarbonyl, or R³⁹And R⁴⁰
Together with C₂~ C_FiveTo form an alkylene chain
Therefore, even if a 3- to 6-membered ring is formed with the nitrogen atom to be bonded,
Well, at this time, this alkylene chain is an oxygen atom or a sulfur source.
May contain 0 to 2 children, and halogen atom or methyl
Optionally substituted with a halogen atom, Z is a halogen atom.
Child, cyano, nitro, C₁~ C₆Alkyl, C₁~ C₆Halo al
Kill, C₁~ C₆Hydroxyalkyl, C₁~ C_FourAlkoxy (C
₁~ C_Four) Alkyl, C₁~ C_FourAlkoxycarbonyl (C₁~ C_Four)
Alkyl, C₂~ C₆Alkenyl, C₂~ C₆Haloalkenyl,
C₂~ C₆Alkynyl, C₂~ C₆Haloalkynyl, C₁~ C₆Al
Coxy, C₁~ C₆Haloalkoxy, C₁~ C₆Alkylthio,
C₁~ C₆Haloalkylthio, C₁~ C₆Alkylsulfini
Le, C₁~ C₆Haloalkylsulfinyl, C₁~ C₆Alkyl
Sulfonyl, C₁~ C₆Haloalkylsulfonyl, C₁~ C₆A
Rukiruamino, di (C₁~ C₆) Alkylamino, -CHO, C₁~
C₆Alkylcarbonyl, C₁~ C₆Haloalkylcarboni
, -CH = NO (C ₁~ C₆Alkyl), -C (C₁~ C₆Alkyl) = NO
(C₁~ C₆Alkyl), C₁~ C₆Alkoxycarbonyl, C₁~
C₆Haloalkoxycarbonyl, C₁~ C₆Alkylaminoca
Lebonyl, di (C₁~ C₆) Alkylaminocarbonyl or fluorine
Represents penyl, p, p1, p2, p3, q, r1, r2, r3 or r4
When representing an integer of 2 or more, each Z is the same
Or p1 is 2
And if two Zs are adjacent, then two adjacent Zs
Is -CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂C (O)-or -CH₂CH₂CH₂C (=
NO (C₁~ C₆Z) is bound by forming
May form a 6-membered ring with the atom.
A hydrogen atom bonded to a carbon atom is a halogen atom, C₁~ C_FourA
Optionally substituted by alkyl or hydroxyl
, M represents an integer of 1 to 3, and n represents an integer of 1 to 5.
, P represents an integer of 0 to 5, and p1 represents an integer of 0 to 4.
, P2 represents an integer of 0 to 3, and p3 represents an integer of 0 to 2.
, Q is an integer of 0 to 7, r is an integer of 0 to 2
, R1 represents an integer of 0 to 3, and r2 is an integer of 0 to 5.
Represents a number, r3 represents an integer of 0 to 7, r4 represents 0 to 9
Represents the integer. ] A phthalic acid diamide compound represented by
Is the salt.

[2] A pest control agent comprising one or more of the phthalic acid diamide compound or the salt thereof described in [1] above as an active ingredient.

[3] A pesticide characterized by containing one or more of the phthalic acid diamide compound or the salt thereof according to the above [1] as an active ingredient.

[4] An insecticidal or acaricidal agent which comprises, as an active ingredient, one or more of the phthalic acid diamide compound or the salt thereof described in [1] above.

[0019]

DETAILED DESCRIPTION OF THE INVENTION The compounds included in the present invention include:
Depending on the kind of the substituent, geometric isomers of E-form and Z-form may exist, but in the present invention, these E-form, Z-form or E-form are present.
And a mixture containing the Z-form in any proportion. In addition, among the compounds included in the present invention, 1
The present invention includes all optically active substances or racemates, although there may be optically active substances due to the presence of one or two or more asymmetric carbon atoms. Furthermore, the compound of the present invention is
When R ¹ , R ² or R ³ is a hydrogen atom, the presence of a tautomer represented by the following formula may be considered depending on the case, but the present invention also includes those structures.

[0020]

[Chemical 11]

Of the compounds included in the present invention, those which can be converted into acid addition salts by a conventional method include, for example,
Hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and other hydrohalic acid salts, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, and other inorganic acid salts, methanesulfonic acid, ethanesulfone Acids, salts of sulfonic acids such as trifluoromethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid,
Formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid and carboxylic acid salts such as citric acid, It may be a salt of an amino acid such as glutamic acid and aspartic acid.

Alternatively, among the compounds included in the present invention, those which can be converted into metal salts by a conventional method include, for example, salts of alkali metals such as lithium, sodium and potassium, alkaline earth salts such as calcium, barium and magnesium. It can be a metal salt or an aluminum salt.

Specific examples of each substituent shown in the present specification are shown below. Here, n- means normal, i- means iso, s- means secondary, and t- means tertiary.

Examples of the halogen atom in the compound of the present invention include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In addition, the notation of “halo” in the present specification also represents these halogen atoms.

In the present specification, the expression C _a -C _b alkyl represents a linear or branched hydrocarbon group having a carbon number of ab, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl,
3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 -Ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,
3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1- Methylpropyl, 1-ethyl-2-methylpropyl, heptyl, 1-methylhexyl, 5-methylhexyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 4,4-dimethylpentyl, 1-
Ethyl pentyl, 2-ethyl pentyl, 1,1,3-trimethylbutyl, 1,2,2-trimethylbutyl, 1,3,3-trimethylbutyl, 2,2,3-trimethylbutyl, 2,3,3- Trimethylbutyl, 1-n-propylbutyl, 1,1,2,2-tetramethylpropyl, octyl, 1-methylheptyl, 3-methylheptyl,
6-methylheptyl, 2-ethylhexyl, 5,5-dimethylhexyl, 2,4,4-trimethylpentyl, 1-ethyl-1-methylpentyl, nonyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl , 7-methyloctyl, 1-ethylheptyl, 1,1-dimethylheptyl, 6,6-dimethylheptyl, decyl, 1-methylnonyl, 2-methylnonyl, 6-methylnonyl, 1-ethyloctyl, 1-n-propylheptyl ,
Undecyl, 1-methyldecyl, 2-methyldecyl, 8-methyldecyl, 1-ethylnonyl, 1-n-propyloctyl, 1-
n-butylheptyl, dodecyl, 1-methylundecyl, 3-
Specific examples thereof include methylundecyl, 9-methylundecyl, 10-methylundecyl, 1-ethyldecyl, 1-n-propylnonyl, etc., and each is selected within the specified carbon atom number range.

The term "C _a -C _b haloalkyl" used in the present specification means _a straight-chain or branched chain having a carbon number of ab, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a chain hydrocarbon group, where 2
When substituted with one or more halogen atoms, the halogen atoms may be the same or different from each other. For example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, bromodifluoromethyl, 2-fluoroethyl, 1-chloroethyl, 2-chloroethyl, 1-bromoethyl, 2-bromoethyl , 2,2-difluoroethyl, 1,2-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2,- Tetrafluoroethyl, pentafluoroethyl, 2-bromo-2-
Chloroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 2,2-dichloro-1,1,
2-trifluoroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 2-bromopropyl, 3-bromopropyl, 2-bromo-1-methylethyl, 3-iodopropyl, 2,3-dichloro Propyl, 2,3-dibromopropyl,
3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 3-bromo-3,3-difluoropropyl, 3,3-dichloro-
3-fluoropropyl, 2,2,3,3-tetrafluoropropyl, 1-bromo-3,3,3-trifluoropropyl, 2,2,3,3,3
-Pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, heptafluoropropyl, 1,2,
2,2-tetrafluoro-1-trifluoromethylethyl, 2,3
-Dichloro-1,1,2,3,3-pentafluoropropyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 2-chloro
-1,1-dimethylethyl, 4-bromobutyl, 3-bromo-2-methylpropyl, 2-bromo-1,1-dimethylethyl, 2,2-dichloro-1,1-dimethylethyl, 2-chloro-1 -Chloromethyl
-2-methylethyl, 4,4,4-trifluorobutyl, 3,3,3-
Trifluoro-1-methylpropyl, 3,3,3-trifluoro-
2-Methylpropyl, 2,3,4-trichlorobutyl, 2,2,2-trichloro-1,1-dimethylethyl, 4-chloro-4,4-difluorobutyl, 4,4-dichloro-4-fluorobutyl , 4-bromo-
4,4-difluorobutyl, 2,4-dibromo-4,4-difluorobutyl, 3,4-dichloro-3,4,4-trifluorobutyl, 3,3
-Dichloro-4,4,4-trifluorobutyl, 4-bromo-3,3,
4,4-tetrafluorobutyl, 4-bromo-3-chloro-3,4,4-
Trifluorobutyl, 2,2,3,3,4,4-hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,2-trifluoro-1-methyl-1 -Trifluoromethylethyl, 3,3,3-
Trifluoro-2-trifluoromethylpropyl, 2,2,3,
3,4,4,4-heptafluorobutyl, 2,3,3,3-tetrafluoro-2-trifluoromethylpropyl, 1,1,2,2,3,3,4,4-
Octafluorobutyl, nonafluorobutyl, 4-chloro
-1,1,2,2,3,3,4,4-octafluorobutyl, 5-chloropentyl, 3-chloro-2,2-dimethylpropyl, 5-bromopentyl, 1,5-dibromopentyl, 4 , 4,4-trifluoro-2
-Methylbutyl, 4,4,5,5,5-pentafluoropentyl, 5
-Bromo-4,4,5,5-tetrafluoropentyl, 4,4-dichloro-5,5,5-trifluoropentyl, 4,5-dichloro-4,5,5-
Trifluoropentyl, 5-bromo-4-chloro-4,5,5-trifluoropentyl, 4,4,4-trifluoro-4-trifluoromethylbutyl, 3,3,4,4,5,5, 5-heptafluoropentyl, 3,4,4,4-tetrafluoro-3-trifluoromethylbutyl, 2,3,3,4,4,4-hexafluoro-2-trifluoromethylbutyl, 2,4, 5-trichloro-1,1,2,3,3,4,5,5-octafluoropentyl, 6-chlorohexyl, 6-bromohexyl, 4,4-dichloro-2,2-dimethylbutyl, 4,4 , 5,5,6,
6,6-heptafluorohexyl, 4,5,5,5-tetrafluoro
-4-trifluoromethylpentyl, 3,4,4,5,5,5-hexafluoro-3-trifluoromethylpentyl, 4,4,4-trifluoro-3,3-bistrifluoromethylbutyl, 1, 1,2,
2,3,3,4,4,5,5,6,6-dodecafluorohexyl, tridecafluorohexyl, 6-chloro-1,1,2,2,3,3,4,4,5,5 , 6,6
-Dodecafluorohexyl, 7-bromoheptyl, 4,5,5,
6,6,6-hexafluoro-4-trifluoromethylhexyl, 5,5,5-trifluoro-4,4-bistrifluoromethylpentyl, pentadecafluoroheptyl, 8-chlorooctyl, 8-bromooctyl, 7, 7,8,8,8-pentafluorooctyl, 9-bromononyl, 9,9,9-trifluorononyl,
Specific examples include 7,8,8,8-tetrafluoro-7-trifluoromethyloctyl, 10-chlorodecyl, 10-bromodecyl, 11-bromoundecyl, 11,11,11-trifluoroundecyl and 12-bromododecyl. They are given by way of example and are selected within the respective specified number of carbon atoms.

In the present specification, the expression C _a -C _b cycloalkyl represents a cyclic hydrocarbon group having a carbon atoms of ab, and is a monocyclic or composite ring having 3 to 6 members. Structures can be formed. Further, each ring may be optionally substituted with an alkyl group within the specified number of carbon atoms. For example, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 2,3,4-trimethylcyclobutyl, cyclopentyl , 1-methylcyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, 1-ethylcyclopentyl, 2-ethylcyclopentyl, 3-ethylcyclopentyl, 1-n-propylcyclopentyl, 1,2-dimethylcyclopentyl, 1,3-dimethyl Cyclopentyl, 2,2-dimethylcyclopentyl, 2,3-dimethylcyclopentyl, 2,4-dimethylcyclopentyl, 2,5-dimethylcyclopentyl,
3,4-dimethylcyclopentyl, 2,2,4-trimethylcyclopentyl, 2,3,4-trimethylcyclopentyl, 2,4,4-trimethylcyclopentyl, cyclohexyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl , 4-methylcyclohexyl, 1-ethylcyclohexyl, 2-ethylcyclohexyl, 4-ethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3 , 3-dimethylcyclohexyl, 3,
4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, cis-bicyclo [3.1.
Specific examples thereof include 0] hexan-2-yl, bicyclo [2.1.1] hexan-5-yl, etc., and each is selected within the specified carbon atom number range.

The term "C _a -C _b halocycloalkyl" used herein refers to a cyclic carbon atom having a carbon atoms of ab, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. It represents a hydrogen group and can form a monocyclic or composite ring structure having from 3 to 6 membered rings. At this time, when substituted with two or more halogen atoms, those halogen atoms may be the same as or different from each other, and each ring has an alkyl group within the specified number of carbon atoms. May be replaced arbitrarily. Further, the substitution with a halogen atom may be a ring structure portion, a side chain portion, or both of them. For example, 1-bromocyclopropyl, 2,
2-dichlorocyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dichloro-3,3-dimethylcyclopropyl, 1-bromocyclobutyl, 2,2,3,3-tetrafluorocyclobutyl , 3,4-dibromocyclopentyl, 1-bromocyclohexyl, 2-fluorocyclohexyl, 2-chlorocyclohexyl, 3-chlorocyclohexyl, 4-chlorocyclohexyl, 2,2,6,6-tetrachlorocyclohexyl,
1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl, 2-trifluoromethylcyclohexyl, 3-trifluoromethylcyclohexyl, 4-trifluoromethylcyclohexyl, 2- Trichloromethylcyclohexyl, 3,5-
Specific examples thereof include ditrifluoromethylcyclohexyl, and each is selected within the specified carbon atom number range.

The term "C _a -C _b alkenyl" used in the present specification means _a linear or branched chain having a carbon number of ab and one or more double bonds in the molecule. Represents an unsaturated hydrocarbon group having, for example, vinyl, 1-propenyl, i-propenyl, 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3 -Butenyl, 2-methyl-1-propenyl, 2-methyl-2-
Propenyl, 1,3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1- Methyl-3-butenyl, 3-methyl-1-butenyl, 1,2-
Dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl,
2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3
-Butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3 -Hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1- (i-butyl) vinyl, 1-ethyl-1-methyl-2-propenyl, 1- Ethyl-2-methyl-2-propenyl, 1- (i-propyl) -2-propenyl, 2-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3- Dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3- Butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl, 2,4-hexadienyl, 1-heptenyl, 1-butyl-2-
Propenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 5-heptenyl, 6-heptenyl, 1-ethyl-4-pentenyl, 3-methyl-1-hexenyl, 1- (i-propyl) -2-butenyl, 1- (i-propyl) -3-butenyl, 1,2-dimethyl-2-pentenyl, 1,1-dimethyl-4-pentenyl, 1,3-dimethyl-
4-pentenyl, 1,4-dimethyl-4-pentenyl, 1-ethyl-
1-methyl-3-butenyl, 1-ethyl-3-methyl-3-butenyl, 2-ethyl-1-pentenyl, 2,2-dimethyl-4-pentenyl, 1,1,2-trimethyl-3-butenyl, 1,1,3-trimethyl-
3-butenyl, 2,2,3-trimethyl-3-butenyl, 2,4-heptadienyl, 3-methyl-1-vinyl-3-butenyl, 1,3,5-heptatrienyl, 1-octenyl, 1-pentyl- 2-propenyl, 2-octenyl, 3-octenyl, 1-methyl-2-heptenyl, 5-octenyl, 7-octenyl, 1-ethyl-2-methyl-2-pentenyl, 3-methyl-5-heptenyl, 1, 5-dimethyl-4-hexenyl, 1,5-dimethyl-5-hexenyl, 2-ethyl-2-hexenyl, 1- (i-propyl) -3-methyl-3-butenyl, 1-ethyl-1,2- Dimethyl-3-butenyl, 1-ethyl-
1,3-dimethyl-3-butenyl, 3,3,4-trimethyl-4-pentenyl, 2-neopentyl-2-propenyl, 2,4-octadienyl, 2,7-octadienyl, 1- (2-methyl-2 -Propenyl) -2-butenyl, 1- (i-propenyl) -4-pentenyl, 1-
(i-Propenyl) -3-methyl-3-butenyl, 1,1,4-trimethyl-2,4-pentadienyl, 5-methyl-2-methylene-5-hexenyl, 1-nonenyl, 1- (n-hexyl ) -2-Propenyl, 2
-Nonenyl, 1-methyl-1-octenyl, 3-nonenyl, 6-nonenyl, 8-nonenyl, 7-methyl-5-octenyl, 2,6-dimethyl-5-heptenyl, 1,1,5-trimethyl-4 -Hexenyl, 4,4,5-trimethyl-5-hexenyl, 3- (neopentyl) -3-butenyl, 2,4-nonadienyl, 2,6-nonadienyl, 3,6-nonadienyl, 2,6-dimethyl-1 , 5-heptadienyl, 2,4-dimethyl-2,6-heptadienyl, 1,4-dimethyl-1,3,5-heptatrienyl, 1,3-dimethyl-1,4,6-heptatrienyl, 1-decenyl, 4 -Decenyl, 5-decenyl,
7-decenyl, 9-decenyl, 1,2-dimethyl-1-octenyl, 3,7-dimethyl-6-octenyl, 1-ethyl-1,5-dimethyl-4-hexenyl, 3,7-dimethyl-7- Octenyl, 1,1,5-
Trimethyl-6-heptenyl, 5-ethyl-1,1-dimethyl-5-
Hexenyl, 1-ethyl-3,3,4-trimethyl-4-pentenyl, 2- (i-propyl) -5-methyl-4-hexenyl, 2-allyl
-5-methyl-4-hexenyl, 1,1,4-trimethyl-2-vinyl-
3-pentenyl, 1-methylene-3-nonenyl, 2,4-decadienyl, 1-methyl-1,3-nonadienyl, 5,9-decadienyl, 1,5-dimethyl-1-vinyl-4-hexenyl, 3, 7-dimethyl-2,6-octadienyl, 1-ethyl-1,5-dimethyl-2,4-
Hexadienyl, 1- (i-propenyl) -4-methyl-3,5-hexadienyl, 1-undecenyl, 2-undecenyl, 4-undecenyl, 10-undecenyl, 1,3,7-trimethyl-6-octenyl, 2, 4-undecadienyl, 5,10-undecadienyl, 2,5,8-undecatrienyl, 1-dodecenyl, 2-dodecenyl, 5-dodecenyl, 7-dodecenyl, 8-dodecenyl,
9-dodecenyl, 10-dodecenyl, 11-dodecenyl, 1-ethyl-3,7-dimethyl-6-octenyl, 1-ethyl-3,7-dimethyl-7-octenyl, 2,4-dodecadienyl, 5,7- Specific examples thereof include dodecadienyl, 8,10-dodecadienyl and the like, and each is selected within the specified number of carbon atoms.

In the present specification, the expression C _a -C _b haloalkenyl represents a straight-chain or C _a -C _b haloalkenyl in which a hydrogen atom bonded to a carbon atom is optionally substituted by a halogen atom, It represents an unsaturated hydrocarbon group which is branched and has one or more double bonds in the molecule, and when it is substituted with two or more halogen atoms, those halogen atoms are They may be the same or different from each other. For example, 2-chlorovinyl, 2-bromovinyl, 2-iodovinyl, 2,2-dichlorovinyl, 2,
2-dibromovinyl, 3-bromo-2-propenyl, 1-chloromethylvinyl, 2-bromo-1-methylvinyl, 1-trifluoromethylvinyl, 3,3,3-trichloro-1-propenyl, 3
-Bromo-3,3-difluoro-1-propenyl, 2-chloro-3,3,
3-trichloro-1-propenyl, 2,3,3,3-tetrachloro-1-
Propenyl, 1-trifluoromethyl-2,2-difluorovinyl, 2-chloro-2-propenyl, 2,3,3-trichloro-2-propenyl, 4-bromo-3-chloro-3,4,4-tri Fluoro-1-
Butenyl, 1-bromomethyl-2-propenyl, 3-chloro-2-
Butenyl, 4,4,4-trifluoro-2-butenyl, 4-bromo-
4,4-difluoro-2-butenyl, 3-bromo-3-butenyl, 3,
4,4-trifluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, 3-bromo-2-methyl-2-propenyl, 3,3,3-trifluoro-2-methylpropenyl, 3 -Chloro-4,4,4-trifluoro-2-butenyl, 3,3,3-trifluoro-1-methyl-1-
Propenyl, 3,4,4-trifluoro-1,3-butadienyl,
3,4-dibromo-1-pentenyl, 3,3,4,4,5,5,5-heptafluoro-1-pentenyl, 5,5-difluoro-4-pentenyl,
4,5,5-trifluoro-4-pentenyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl-1-butenyl, 3,5,5-trifluoro-2,4-pentadienyl, 4 , 4,5,5,6,6,6-Heptafluoro-2-hexenyl, 3,4,4,5,5,5-hexafluoro-
3-trifluoromethyl-1-pentenyl, 4,5,5,5-tetrafluoro-4-trifluoromethyl-2-pentenyl, 5-bromo-4,5,5-trifluoro-4-trifluoromethyl- 2-pentenyl, 4,5,5,6,6,6-hexafluoro-4-trifluoromethyl-2-hexenyl, 3-perfluorobutyl-2-propenyl, 3-iodo-2-octenyl, 2-per Fluorohexyl vinyl, 3-perfluorohexyl-2-propenyl, 12-
Bromo-2-dodecenyl and the like can be mentioned as a specific example, and each is selected in the range of the designated carbon atom number.

The term "C _a -C _b alkynyl" used in the present specification means _a straight or branched chain having a carbon number of ab and one or more triple bonds in the molecule. Represents an unsaturated hydrocarbon group having, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl
-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl,
2-methyl-3-butynyl, 1-hexynyl, 1- (n-propyl)-
2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3
-Hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 1- (i-propyl) -2-propynyl, 1,1-dimethyl-2-butynyl, 2,2-dimethyl-3-butynyl, 1-heptinyl, 1- (n-butyl) -2-propynyl, 2
-Heptinyl, 3-heptynyl, 1-methyl-3-hexynyl,
1-ethyl-2-pentynyl, 1-ethyl-3-pentynyl, 6-heptynyl, 1-methyl-1- (n-propyl) -2-propynyl, 1-
(i-Propyl) -1-methyl-2-propynyl, 1- (i-butyl) -2
-Propinyl, 5-methyl-3-hexynyl, 1,1-dimethyl-2
-Pentynyl, 1-ethyl-1-methyl-2-butynyl, 1-octynyl, 1- (n-pentyl) -2-propynyl, 2-octynyl, 3-octynyl, 1-methyl-3-heptynyl, 1-ethyl -
3-hexynyl, 7-octynyl, 1- (n-butyl) -1-methyl-
2-propynyl, 1- (1-methylbutyl) -2-propynyl, 1-
(i-Butyl) -1-methyl-2-propynyl, 2-nonynyl, 3-nonynyl, 1-ethyl-3-heptynyl, 1-methyl-1- (n-pentyl) -2-propynyl, 1- (n -Butyl) -1-methyl-2-butynyl, 1- (n-butyl) -1-ethyl-2-propynyl, 1- (i-pentyl) -1-methyl-2-propynyl, 1-decynyl, 2- Decynyl, 3-decynyl, 5-decynyl, 9-decynyl, 1- (n-hexyl) -1-methyl-2-propynyl, 2-undecynyl, 10-undecynyl, 5,10-undecadiynyl, 3-dodecynyl, 7
Specific examples include -dodecynyl, 9-dodecynyl, 10-dodecynyl, 11-dodecynyl and the like, each of which is selected within the specified number of carbon atoms.

In the present specification, C _a -C _b haloalkynyl represents a straight-chain or C _{a -b} carbon atom having a hydrogen atom bonded to a carbon atom, which is optionally substituted by a halogen atom. It represents an unsaturated hydrocarbon group which is branched and has one or more triple bonds in the molecule, and when it is substituted with two or more halogen atoms, those halogen atoms are mutually They may be the same or different from each other. For example, 2-chloroethynyl, 2-
Bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, 3,3,3-trifluoro-1-propynyl, 3-chloro-1 -Methyl-2-propynyl, 3-bromo-1-methyl-2-propynyl, 3-iodo-1-methyl-2-propynyl, 3-chloro-1,1-
Dimethyl-2-propynyl, 3-bromo-1,1-dimethyl-2-propynyl, 3-iodo-1,1-dimethyl-2-propynyl, 1-chloromethyl-1-methyl-2-butynyl, 4-chloro -2,2-dimethyl-3-butynyl, 4-bromo-2,2-dimethyl-3-butynyl, 4-iodo-2,2-dimethyl-3-butynyl, 10-bromo-9-
Specific examples thereof include decynyl and the like, and each is selected within the specified number of carbon atoms.

The term "C _a -C _b cycloalkenyl" used in the present specification means _a cyclic unsaturated carbonization having a carbon number of ab and having one or more double bonds in the molecule. It represents a hydrogen group and can form a monocyclic or composite ring structure having from 3 to 6 membered rings. Further, each ring may be optionally substituted with an alkyl group within the specified number of carbon atoms, and at this time, the double bond may be present in the ring or in the substituent. For example, 2-vinylcyclopropyl, 3,3-dimethyl-2- (2-methyl-1-propenyl) cyclopropyl, cyclopenten-1-yl, 2-cyclopentene-
1-yl, 3-cyclopenten-1-yl, 3-methylenecyclopentyl, 2-allylcyclopentyl, cyclohexene-1
-Yl, 2-cyclohexen-1-yl, 3-cyclohexene-1
-Yl, 4-methylenecyclohexyl, 3-methyl-2-cyclohexen-1-yl, 2-methyl-2-cyclohexen-1-yl, 1-methyl-2-cyclohexen-1-yl, 4-methyl-3-
Cyclohexen-1-yl, 1-methyl-3-cyclohexene-1
-Yl, 6-methyl-3-cyclohexen-1-yl, 6-methyl-
2-methylenecyclohexyl, 2-ethyl-3-cyclohexen-1-yl, 4,6-dimethyl-3-cyclohexen-1-yl, 2
-Methyl-2,5-cyclohexadien-1-yl, bicyclo [2.
2.1] -5-Hepten-2-yl, 2-methylbicyclo [2.2.1] -5-
Specific examples thereof include hepten-2-yl and the like, and each is selected within the specified number of carbon atoms.

In the present specification, the expression C _a -C _b halocycloalkenyl refers to a ring having a carbon number of _a to _b , in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, In addition, it represents an unsaturated hydrocarbon group having one or two or more double bonds in the molecule, and can form a monocyclic or complex cyclic structure of a 3-membered ring to a 6-membered ring.
Further, each ring may be optionally substituted with an alkyl group within the specified number of carbon atoms, and at this time, the double bond may be present in the ring or in the substituent. Furthermore, when substituted by two or more halogen atoms, those halogen atoms may be the same as or different from each other. For example, 2- (2,2-dichlorovinyl) -3,3-dimethylcyclopropyl, 2- (2-chloro-3,3,
3-trifluoro-1-propenyl) -3,3-dimethylcyclopropyl, 2-chlorobicyclo [2.2.1] -5-hepten-2-yl and the like are mentioned as specific examples, and the number of carbon atoms designated by each is specified. The range is selected.

In the present specification, the expression C _a -C _b alkoxy represents a linear or branched alkyl-O-group having a carbon number of ab, for example, methoxy, ethoxy, n-.
Propyloxy, i-propyloxy, n-butyloxy,
s-Butyloxy, i-butyloxy, t-butyloxy, n-
Pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1-ethylpropyloxy, 1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, neopentyloxy, n-hexyl Oxy,
Specific examples include 1,1-dimethylbutyloxy,
Each is selected within the specified number of carbon atoms.

In the present specification, the expression C _a -C _b haloalkoxy means that a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, which is a straight chain having a carbon number of ab or When it represents a branched alkyl-O- group and is substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. For example difluoromethoxy,
Trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2,-
Tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2,2-dichloro-1,1,2-trifluoroethoxy, 2,2,2-trichloro-1,1-difluoroethoxy, 2 -Bromo-1,1,2,2-tetrafluoroethoxy, 2-chloropropyloxy, 3-chloropropyloxy, 2,2,2-trifluoro-1-trifluoromethylethoxy, 2,2,3,3 -Tetrafluoropropyloxy, 1,1,2,3,3,3-hexafluoropropyloxy, 2-bromo-1,1,2,3,3,3-hexafluoropropyloxy and the like are mentioned as specific examples. , Selected within the specified number of carbon atoms.

In the present specification, the expression C _a -C _b alkylthio represents a linear or branched alkyl-S- group having a carbon number of ab, for example methylthio, ethylthio, n-. Propylthio, i-propylthio, n-butylthio,
s-Butylthio, i-butylthio, t-butylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-
Specific examples include methylbutylthio, 1-ethylpropylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, neopentylthio, and n-hexylthio.
Each is selected within the specified number of carbon atoms.

In the present specification, the expression C _a -C _b haloalkylthio means that a hydrogen atom bonded to a carbon atom is optionally substituted by a halogen atom, and has a straight chain structure of a to b carbon atoms or When the alkyl-S- group has a branched chain structure and is substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. For example, difluoromethylthio, trifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 1,1,2-trifluoro-2-chloroethylthio , Pentafluoroethylthio, 2-bromo-1,1,
Specific examples include 2,2-tetrafluoroethylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-trifluoromethylethylthio, nonafluorobutylthio, and the like. It is selected in the range of the number of atoms.

In the present specification, the expression C _a -C _b alkylsulfinyl represents a linear or branched alkyl-S (O)-group having a carbon number of ab, for example methylsulfinyl. , Ethylsulfinyl and the like are mentioned as specific examples, and each is selected within the specified number of carbon atoms.

In the present specification, the term "C _a -C _b haloalkylsulfinyl" means that a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the number of carbon atoms is a.
~ B represents a linear or branched alkyl-S (O)-group, wherein when substituted with two or more halogen atoms, those halogen atoms are the same as each other, or They may be different from each other. For example, difluoromethylsulfinyl, trifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-bromo-1,1,2,2-tetrafluoroethylsulfinyl, 1,2,2,2 -Tetrafluoro-1-trifluoromethylethylsulfinyl, nonafluorobutylsulfinyl and the like are mentioned as specific examples, and each is selected within the specified carbon atom number range.

In the present specification, the expression C _a -C _b alkylsulfonyl represents a linear or branched alkyl-S (O) ₂ -group having a carbon number of ab, such as methane. Specific examples thereof include sulfonyl, ethanesulfonyl, n-propanesulfonyl and the like, and each is selected within the specified carbon atom number range.

In the present specification, the expression C _a -C _b haloalkylsulfonyl means that a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and the number of carbon atoms is ab.
Represents a straight-chain or branched-chain alkyl-S (O) ₂ -group consisting of two or more halogen atoms which are the same or different from each other when they are substituted by two or more halogen atoms. It may be different. For example, difluoromethanesulfonyl, trifluoromethanesulfonyl,
Specific examples include 2,2,2-trifluoroethanesulfonyl, 1,1,2,2-tetrafluoroethanesulfonyl, and 1,1,2-trifluoro-2-chloroethanesulfonyl. It is selected in the range of the number of atoms.

C in the present specification_a~ C_bAlkyl Carboni
The notation of a straight chain is a straight-chain or
Represents a branched alkyl-C (O)-group, such as CH₃C (O)-, C₂H_Five
C (O)-, n-C₃H₇C (O)-, (CH₃)₂CHC (O)-, C₂H_FiveCH (CH₃) C (O)
-, (CH₃)₂CHCH₂C (O)-, t-C_FourH ₉C (O)-, n-C₆H₁₃C (O) -etc
As a specific example, the range of the number of carbon atoms specified for each
Selected in.

In the present specification, the term "C _a -C _b haloalkylcarbonyl" means that a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom and the number of carbon atoms is ab.
Represents a straight-chain or branched-chain alkyl-C (O)-group consisting of two or more halogen atoms, which are the same or different from each other when substituted with two or more halogen atoms. It may be. For example ClCH ₂ C
(O)-, Cl ₂ CHC (O)-, CCl ₃ C (O)-, CF ₃ C (O)-, C ₂ F ₅ C (O)-,
Specific examples thereof include nC ₃ F ₇ C (O)-, ClCH ₂ CH ₂ CH ₂ C (O)-, etc., and each is selected within the specified carbon atom number range.

C in the present specification_a~ C_bAlkoxy carbo
The notation of nil refers to a straight-chain or
Represents a branched alkyl-O-C (O)-group, for example CH₃OC (O)
-, C₂H _FiveOC (O)-, n-C₃H₇OC (O)-, (CH₃)₂CHOC (O)-, n-C_Four
H₉OC (O)-, (CH₃)₂CHCH₂OC (O)-, t-C_FourH₉OC (O) -etc is concrete
For example, select within the specified number of carbon atoms.
Is selected.

In the present specification, the notation C _a -C _b haloalkoxycarbonyl means that the number of carbon atoms is a, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
~ B represents a straight-chain or branched-chain alkyl-OC (O)-group, wherein when substituted by two or more halogen atoms, those halogen atoms are the same or mutually It may be different. For example ClCH ₂ C
H ₂ OC (O)-, CF ₃ CH ₂ OC (O)-and the like are mentioned as specific examples, and each is selected within the specified carbon atom number range.

In the present specification, the expression C _a -C _b cyanoalkyl refers to a straight-chain or branched chain having a carbon number of ab, in which a hydrogen atom bonded to a carbon atom is optionally substituted with cyano. Represents a chain alkyl group, for example NCCH _2- , NC
_{CH 2 CH 2 -, CH 3} CH (CN) -, NCCH 2 CH 2 CH 2 -, NCC (CH 3) 2 -, NC
_{(CH 2) 4 -, NCCH} 2 C (CH 3) 2 -, NCC (CH 3) (C 2 H 5) -, NCC (C 2 H 5)
_2- , NC (CH ₂ ) _6- and the like are mentioned as specific examples, and each is selected within the specified number of carbon atoms.

C in the present specification_a~ C_bAlkylamino
The notation is a straight or branched chain consisting of a to b carbon atoms.
Represents an alkyl-NH- group of the formula₃NH-, C₂H_FiveNH-, n
-C₃H ₇NH-, i-C₃H₇NH-, n-C_FourH₉NH-, i-C_FourH₉NH-, t-C_FourH₉N
H- etc. are mentioned as specific examples, and the number of carbon atoms specified for each
The range is selected.

In the present specification, the expression di (C _a -C _b ) alkylamino means a linear or branched alkyl group in which a hydrogen atom bonded to a nitrogen atom has a carbon atom number of ab. Both represent substituted> N-groups, the alkyl groups of which may be identical to one another or different from one another. For example _{(CH 3) 2 N-, C} 2 H 5 N (CH 3)
-, (C ₂ H ₅ ) ₂ N-, nC ₃ H ₇ N (CH ₃ )-, iC ₃ H ₇ N (CH ₃ )-, (nC ₃ H
₇ ) ₂ N-, nC ₄ H ₉ N (CH ₃ )-, iC ₄ H ₉ N (CH ₃ )-, tC ₄ H ₉ N (CH ₃ )-
Etc. are mentioned as a specific example, and each is selected within the range of the designated carbon atom number.

The term "C _a -C _b alkylaminocarbonyl" used in the present specification means that a hydrogen atom bonded to a nitrogen atom is substituted by a linear or branched alkyl group having a carbon number of ab. Represented by --NH--C (O)-group, for example CH ₃
NHC (O)-, C ₂ H ₅ NHC (O)-, nC ₃ H ₇ NHC (O)-, iC ₃ H ₇ NHC (O)
-, NC ₄ H ₉ NHC (O)-, iC ₄ H ₉ NHC (O)-, tC ₄ H ₉ NHC (O)-, etc. are listed as specific examples, and each can be selected within the specified number of carbon atoms. To be done.

In the present specification, the notation of di (C _a -C _b ) alkylaminocarbonyl means that a hydrogen atom bonded to a nitrogen atom is a straight-chain or branched-chain alkyl having a carbon number of ab. By groups, both represent> NC (O)-groups, both substituted, the alkyls of which may be identical to one another or different from one another. For example (CH ₃ ) ₂ NC
(O)-, C ₂ H ₅ N (CH ₃ ) C (O)-, (C ₂ H ₅ ) ₂ NC (O)-, etc. are mentioned as specific examples, and within the range of the number of carbon atoms specified for each. To be selected.

In the present specification, the expression C _a -C _b alkylaminothiocarbonyl means that the hydrogen atom bonded to the nitrogen atom is a linear or branched alkyl group having a carbon number of ab. substituted -NH-C (S) - represents a group such _{CH 3 NHC (S) -,} C 2 H 5 NHC (S) -, nC 3 H 7 NHC (S) -, iC 3 H 7
NHC (S)-, nC ₄ H ₉ NHC (S)-, iC ₄ H ₉ NHC (S)-, tC ₄ H ₉ NHC
(S)-and the like are mentioned as specific examples, and each is selected within the range of the designated carbon atom number.

In the present specification, the notation of di (C _a -C _b ) alkylaminothiocarbonyl means that the hydrogen atom bonded to the nitrogen atom is a linear or branched chain having a carbon number of ab. > NC (S)-both substituted with an alkyl group
And the alkyls may be the same or different from each other. For example (CH ₃ ) ₂ NC
(S)-, C ₂ H ₅ N (CH ₃ ) C (S)-, (C ₂ H ₅ ) ₂ NC (S)-, etc. are mentioned as specific examples, and within the specified number of carbon atoms. To be selected.

In the present specification, the notation of benzyl which may be substituted by (Z) _p is the same or different from each other, Z represents a benzyl group bonded to a carbon atom forming a benzene ring. Represent

In the present specification, C _{a to} C _b cycloalkyl (C
_d ~ C _e ) alkyl, C _a ~ C _b alkoxy (C _d ~ C _e ) alkyl,
C _{a to} C _b alkylthio (C _{d to} C _e ) alkyl, C _{a to} C _b alkoxycarbonyl (C _{d to} C _e ) alkyl, C _{a to} C _b haloalkoxycarbonyl (C _{d to} C _e ) alkyl or (Z ) The notation such as (C _d -C _e ) alkyl substituted by phenyl which may be substituted by _p may be any C _a-
C _b cycloalkyl group, C _{a to} C _b alkoxy group, C _{a to} C _b alkylthio group, C _{a to} C _b alkoxycarbonyl group, C _{a to} C _b haloalkoxycarbonyl group or (Z) _p . A phenyl group also represents a linear or branched hydrocarbon group in which a hydrogen atom bonded to a carbon atom is optionally substituted and has d to e carbon atoms. The range is selected.

R in the present specification^FiveArbitrarily replaced by
(C_d~ C_e) Alkyl, R¹⁶Arbitrarily replaced by
(C_d~ C_e) Alkyl, R²⁸Arbitrarily replaced by (C_d~
C_e) Alkyl, R³²Arbitrarily replaced by (C_d~ C_e)
Rukiru or R³⁵Arbitrarily replaced by (C_d~ C_e) Al
The notation of kill is that a hydrogen atom bonded to a carbon atom is
R^FiveBase, R¹⁶Base, R²⁸Base, R³²Group or R³⁵Set by the group
A straight chain or branched chain having d to e carbon atoms
Represents a chain hydrocarbon group, where each (C _d~ C_e)
Substituent R on Rukiru^Five, R¹⁶, R²⁸, R³²Or R³⁵2 or more
Each R when present^Five, R¹⁶, R²⁸, R³²Or R³⁵Is
They may be the same as or different from each other.

[0057] herein is optionally substituted by R ⁵ (C _d ~C _e) alkenyl, optionally substituted by R ¹⁶ (C _d ~C _e) alkenyl, optionally substituted by R ²⁸
(C _d ~C _e) alkenyl, optionally substituted by R ³² (C _d
~ C _e ) alkenyl or R ³⁵ optionally substituted (C _d
~ C _e ) alkenyl represents a hydrogen atom bonded to a carbon atom, optionally substituted by any R ⁵ group, R ¹⁶ group, R ²⁸ group, R ³² group or R ³⁵ group, the number of carbon atoms _d to _e represents a straight-chain or branched-chain unsaturated hydrocarbon group having one or two or more double bonds in the molecule, wherein each (C _{d to} C _e ) Substituents on alkenyl R ⁵ , R ¹⁶ , R ²⁸ , R
When two or more ³² or R ³⁵ are present, each R ⁵ ,
R ¹⁶ , R ²⁸ , R ^{32 and} R ³⁵ may be the same or different from each other.

[0058] herein is optionally substituted by R ⁵ (C _d ~C _e) alkynyl, optionally substituted by R ¹⁶ (C _d ~C _e) alkynyl, optionally substituted by R ²⁸
(C _d ~C _e) alkynyl, optionally substituted by R ³² (C _d
~ C _e ) alkynyl or R ³⁵ optionally substituted (C _d
~ C _e ) alkynyl is represented by a hydrogen atom bonded to a carbon atom, optionally substituted by any R ⁵ group, R ¹⁶ group, R ²⁸ group, R ³² group or R ³⁵ group, the number of carbon atoms is _{d- e} represents a straight or branched chain unsaturated hydrocarbon group having 1 or 2 or more triple bonds in the molecule, wherein each (C _d -C _e ) alkynyl The above substituents R ⁵ , R ¹⁶ , R ²⁸ , R
When two or more ³² or R ³⁵ are present, each R ⁵ ,
R ¹⁶ , R ²⁸ , R ^{32 and} R ³⁵ may be the same or different from each other.

[0059] representation of the substituted (C _d ~C _e) alkoxycarbonyl by phenyl which is substituted in the present specification by (Z) _p is the phenyl group which may be substituted by (Z) _p Represents a (C _d -C _e ) alkoxycarbonyl group having the above-mentioned meaning in which a hydrogen atom bonded to a carbon atom is optionally substituted, and is selected within the range of the number of designated carbon atoms.

The compound of the present invention can be produced, for example, by the following method. Manufacturing method A

[0061]

[Chemical 12]

General formula (2) [wherein V ¹ , V ² , V ³ , V ⁴ ,
W ¹ , W ² , X ¹ , X ² , Y, m and n have the same meanings as described above. ] The compound represented by these, and general formula (3) [In formula, R < ¹ > and R < ² > represent the same meaning as the above. ] In the solvent inert to the reaction or in the absence of a solvent, if necessary in the presence of a catalyst, R ³ in the general formula (1) is a hydrogen atom. Certain general formula (1-1)
[Wherein V ¹ , V ² , V ³ , V ⁴ , W ¹ , W ² , X ¹ , X ² , Y, R ¹ , R ² ,
m and n have the same meanings as described above. ] The compound of the present invention represented by

The amount of the reaction substrate is the same as that of the compound 1 of the general formula (2).
The compound of the general formula (3) can be used in an amount of 1 to 50 equivalents relative to the equivalent amount.

When a solvent is used, any solvent may be used as long as it does not inhibit the progress of the reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic hydrocarbons such as hexane and heptane. Alicyclic hydrocarbons such as cyclohexane, aromatic halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene,
Aliphatic halogenated hydrocarbons such as tetrachloroethylene, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, ethers such as 1,4-dioxane, ethyl acetate, esters such as ethyl propionate, dimethylformamide, dimethylacetamide, Amides such as N-methyl-2-pyrrolidone, formic acid, acetic acid, carboxylic acids such as propionic acid, triethylamine, tributylamine, N,
Amines such as N-dimethylaniline, pyridines such as pyridine and picoline, alcohols such as methanol, ethanol and ethylene glycol, acetonitrile, dimethyl sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and water Can be mentioned. These solvents may be used alone or in combination of two or more.

When a catalyst is used, the reaction catalyst is
For example, mineral acids such as hydrochloric acid, sulfuric acid and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid, amines such as triethylamine hydrochloride and pyridine hydrochloride 0.001 to 1 equivalent of Lewis acid such as acid addition salts of zinc, zinc chloride, titanium tetrachloride, cerium chloride, ytterbium triflate, and boron trifluoride-ether complex is used with respect to the compound of general formula (2). be able to.

The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set arbitrarily.

Generally, for example, 1 to 10 equivalents of the compound of the general formula (3) is used with respect to 1 equivalent of the compound of the general formula (2), without solvent, or with tetrahydrofuran, 1,4-dioxane or the like. It is preferable to carry out the reaction in a temperature range of 50 ° C. to the reflux temperature of the reaction mixture for 30 minutes to 24 hours using a solvent. Manufacturing method B

[0068]

[Chemical 13]

R in the general formula (1)³Is a hydrogen atom
General formula (1-1) [in the formula, V¹, V², V ³, V^Four, W¹, W², X¹,
 X², Y, R¹, R², m and n have the same meanings as described above. ]so
The compound of the present invention represented by the general formula (4) [in the formula, R³Is water
Represents the same meaning as above except for elementary atoms, J¹Is a chlorine atom, odor
Elemental atom, iodine atom, C₁~ C_FourAlkyl carbonyloxy
(Eg pivaloyloxy), C₁~ C_FourAlkyl sulfo
Nate (eg, methanesulfonyloxy), C₁~ C_FourHa
Roalkyl sulfonates (eg trifluoromethane
Sulfonyloxy), aryl sulfonates (eg,
Benzenesulfonyloxy, p-toluenesulfonyloxy
Si) or azolyl (eg, imidazol-1-yl)
Represents such a good leaving group. ] And a compound represented by
If necessary, in the presence of a base,
By reacting with an active solvent, the general formula
(1) [wherein V¹, V², V³, V^Four, W¹, W², X¹, X², Y, m
And n have the same meanings as described above. ] In R³Is hydrogen
It is possible to obtain the compound of the present invention which is a substituent other than
It

Regarding the amount of the reaction substrate, 1 to 50 equivalents of the compound of the general formula (4) can be used with respect to 1 equivalent of the compound of the general formula (1-1).

When a solvent is used, any solvent may be used as long as it does not inhibit the progress of the reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic hydrocarbons such as hexane and heptane. Alicyclic hydrocarbons such as cyclohexane, aromatic halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene,
Aliphatic halogenated hydrocarbons such as tetrachloroethylene, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, ethers such as 1,4-dioxane, ethyl acetate, esters such as ethyl propionate, dimethylformamide, dimethylacetamide, Amides such as N-methyl-2-pyrrolidone, triethylamine, tributylamine, amines such as N, N-dimethylaniline, pyridine,
Pyridine and other pyridines, methanol, ethanol, ethylene glycol and other alcohols, acetonitrile,
Dimethyl sulfoxide, sulfolane, 1,3-dimethyl-2-
Examples include imidazolidinone and water. These solvents may be used alone or in combination of two or more.

When a base is used, examples of the base to be used include alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium ethoxide and potassium tertiary. Alkali metal alkoxides such as leaf butoxide, lithium diisopropylamide, lithium hexamethyldisilazane, alkali metal amides such as sodium amide, organic metal compounds such as tertiary butyllithium, alkalis such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate. Metal carbonate, triethylamine,
Tributylamine, N, N-dimethylaniline, pyridine,
An organic base such as 4- (dimethylamino) pyridine, imidazole or 1,8-diazabicyclo [5,4,0] -7-undecene is used in an amount of 1 to 4 equivalents based on the compound of the general formula (1-1). be able to.

The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set arbitrarily.

Generally, for example, 1 to 10 equivalents of the compound of the general formula (4) is used per 1 equivalent of the compound of the general formula (1-1), and in a polar solvent such as tetrahydrofuran or dimethylformamide, if necessary. For example, sodium hydride, potassium hydride, potassium tert-butoxide, potassium hydroxide, etc. are used as a base in an amount of 1 to 3 equivalents relative to 1 equivalent of the compound of the general formula (1-1), and in a temperature range of 0 to 90 ° C. It is preferable to carry out the reaction for 10 minutes to 24 hours. Manufacturing method C

[0075]

[Chemical 14]

General formula (5) [wherein V ¹ , V ² , V ³ , V ⁴ ,
W ² , X ¹ , X ² , Y, R ³ , m and n have the same meanings as described above. ] The compound represented by these, and general formula (3) [In formula, R < ¹ > and R < ² > represent the same meaning as the above. ] In the solvent inert to the reaction or in the absence of a solvent, if necessary in the presence of a base, using a condensing agent to react with the compound represented by the formula (1) General formula (1-2) in which ¹ is an oxygen atom [wherein V ¹ , V ² , V ³ , V ⁴ , W ² , X ¹ , X ² , Y,
R ¹ , R ² , R ³ , m and n have the same meanings as described above. ] The compound of the present invention represented by

The amount of the reaction substrate is the amount of the compound 1 of the general formula (5).
The compound of the general formula (3) can be used in an amount of 1 to 100 equivalents relative to the equivalent amount.

The condensing agent is not particularly limited as long as it is used in ordinary amide synthesis. For example, Mukaiyama reagent (2-chloro-N-methylpyridinium iodide), DCC (1,3
-Dicyclohexylcarbodiimide), WSC (1-ethyl-3
-(3-Dimethylaminopropyl) -carbodiimide hydrochloride), CDI (carbonyldiimidazole), dimethylpropynylsulfonium bromide, propargyltriphenylphosphonium bromide, DEPC (diethyl cyanophosphate), etc. to the compound of general formula (5) 1 to 4
An equivalent amount can be used.

When a solvent is used, any solvent may be used so long as it does not inhibit the progress of the reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene, and aliphatic hydrocarbons such as hexane and heptane. Alicyclic hydrocarbons such as cyclohexane, aromatic halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane, trichloroethylene,
Aliphatic halogenated hydrocarbons such as tetrachloroethylene, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, ethers such as 1,4-dioxane, ethyl acetate, esters such as ethyl propionate, dimethylformamide, dimethylacetamide, Amides such as N-methyl-2-pyrrolidone, triethylamine, tributylamine, amines such as N, N-dimethylaniline, pyridine,
Examples thereof include pyridines such as picoline, acetonitrile, dimethyl sulfoxide, and the like. These solvents may be used alone or in combination of two or more.

Although the addition of a base is not always necessary, when a base is used, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, triethylamine. An organic base such as tributylamine, N, N-dimethylaniline, pyridine, 4- (dimethylamino) pyridine, imidazole, 1,8-diazabicyclo [5,4,0] -7-undecene, etc. 1 to 4 equivalents relative to the compound of 1).

The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually in the range of 5 minutes to 100 hours. Can be set arbitrarily.

Generally, for example, 1 to 20 equivalents of the compound of the general formula (3) and 1 to 4 equivalents of WSC (1-ethyl-3- (3- Dimethylaminopropyl) -carbodiimide hydrochloride), CDI (carbonyldiimidazole) and other condensing agents are used, if necessary 1 to 4 equivalents of potassium carbonate, triethylamine, pyridine, 4-
In the presence of a base such as (dimethylamino) pyridine, using no solvent or a solvent such as dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, etc., in the range of 0 ° C to the reflux temperature of these solvents. 10,
It is preferable to carry out the reaction for from minutes to 24 hours. Manufacturing method D

[0083]

[Chemical 15]

General formula (6) [wherein X ¹ , X ² , W ¹ , R ¹ , R ²
And m have the same meaning as described above. And a compound represented by the general formula (7) [in the formula, V ¹ , V ² , V ³ , V ⁴ , Y, R ³ and n
Represents the same meaning as described above. A compound represented by, by similar conditions reaction and Process C, the general formula W ² is an oxygen atom in the general formula (1) (1-3)
[Wherein V ¹ , V ² , V ³ , V ⁴ , W ¹ , X ¹ , X ² , Y, R ¹ , R ² , R ³ ,
m and n have the same meanings as described above. ] The compound of the present invention represented by Manufacturing method E

[0085]

[Chemical 16]

General formula (8) [wherein V ¹ , V ² , V ³ , V ⁴ ,
W ² , X ¹ , X ² , Y, m and n have the same meanings as described above. ] The compound represented by these, and general formula (3) [In formula, R < ¹ > and R < ² > represent the same meaning as the above. ] The compound represented by
By reacting under the same conditions as in A, general formula (1)
In formula (1-4), wherein W ¹ is an oxygen atom and R ³ is a hydrogen atom [wherein V ¹ , V ² , V ³ , V ⁴ , W ² , X ¹ ,
X ² , Y, R ¹ , R ² , m and n have the same meanings as described above. ] The compound of the present invention represented by Manufacturing method F

[0087]

[Chemical 17]

General formula (9) [wherein W ¹ , X ¹ , X ² , R ¹ and
m has the same meaning as above. And a compound represented by the general formula (7): [wherein V ¹ , V ² , V ³ , V ⁴ , Y, R ³ and n have the same meanings as described above]. ] The compound represented by
By reacting under the same conditions as in the general formula (1), W ² is an oxygen atom and R ² is a hydrogen atom in the general formula (1-5) [wherein V ¹ , V ² , V ³ , V ⁴ , W ¹ , X ¹ , X ² ,
Y, R ¹ , R ³ , m and n have the same meanings as described above. ] The compound of the present invention represented by

In Processes A to F, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water and concentrated, or poured into ice water and subjected to usual post-treatments such as extraction with an organic solvent and concentration. The target compound of the present invention can be obtained. When purification is required, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography, and liquid chromatography fractionation.

In Production Method A, the compound represented by the general formula (2), which is a starting material compound for producing the compound of the present invention, can be synthesized by the following method.

(A). In the general formula (2), X ¹ is X ¹ -1 or X.
General formula (2-1) that is ¹ -4 [wherein V ¹ , V ² , V ³ , V ⁴ , W
¹ , W ² , X ² , Y, m and n have the same meanings as described above. ] The manufacture of the compound represented by these.

[0092]

[Chemical 18]

General formula (10) [wherein V ¹ , V ² , V ³ , V ⁴ ,
W ¹ , W ² , X ² , Y, m and n have the same meanings as described above. ], A known method described in the literature, for example, Journal of the American Chemical Society [J. Am. Chem. Soc.] 1947, 69, 194.
Page 6, Chemistry Letters [Chem. Lett.] 197
4th year, p. 701, Journal of Heterocyclic Chemistry [J. Heterocyclic Chem.] 1988
Annually, 25 volumes, page 1003 and the like can be reacted to obtain a compound represented by the general formula (2-1) in which X ¹ is X ¹ -1.

Further, the compound represented by the general formula (10) can be prepared by, for example, Chemiste Berichte [Chem. Ber.] 1966.
1999, p. 850, The Journal of Organic Chemistry [J. Org. Chem.] 1995,
60, 468, Justus Liebigs Ann. Chem., 1969
, 725, page 29, etc., to give a compound represented by the general formula (2-1) in which X ¹ is X ¹ -4.

Some of the compounds represented by the general formula (10) used as starting materials in these reactions are known compounds, and other compounds are general methods for synthesizing anilines described in the literature. It can be easily synthesized from the corresponding substituted phthalimide derivative according to

(B). In the general formula (2), X ¹ is X ¹ -2, X ^1-
3, the general formula (2-2) which is X ¹ -6 or X ¹ -7 [wherein V ¹ , V
² , V ³ , V ⁴ , W ¹ , W ² , X ² , Y, m and n have the same meanings as described above. ] The manufacture of the compound represented by these.

[0097]

[Chemical 19]

General formula (11) [wherein V ¹ , V ² , V ³ , V ⁴ ,
W ¹ , W ² , X ² , Y, m and n represent the same meaning as described above, J ² is a bromine atom, an iodine atom, a C ₁ -C ₄ haloalkyl sulfonate (for example, trifluoromethanesulfonyloxy) or -B ( OH) ₂ etc. ] The compound and general formula (1
2) [wherein X ¹ represents X ¹ -2, X ¹ -3, X ¹ -6 or X ¹ -7, and J ³
Is a bromine atom, an iodine atom, a C ₁ -C ₄ haloalkyl sulfonate (for example, trifluoromethanesulfonyloxy), a tri (C ₁ -C ₄ ) alkylstannyl (for example, —Sn (Bu
-n) ₃ ) or -B (OH) ₂ etc. ], A known method described in literature, for example, tetrahedron letters [Tetrahedron Lett.], 1994, 35, 2
405, 1995, 36, 1679 and 199.
6 years, 37, 3247, etc., to give a compound of the general formula (2-2) by cross-coupling reaction.
[In the formula, V ¹ , V ² , V ³ , V ⁴ , W ¹ , W ² , X ² , Y, m and n represent the same meaning as described above, and X ¹ represents X ¹ -2, X ¹ -3 , X ¹ -6 or X ¹ -7. ] The compound represented by these can be obtained.

[0099] In general formula X ¹ is X ¹ -6 or X ¹ -7 in the compound represented by the general formula (2-2) (2-3) [wherein, V ^1, V ^2, V ³ , V ⁴ , W ¹ , W ² , X ² , Y, m and n have the same meanings as described above. ] Another method for obtaining the compound represented by

[0100]

[Chemical 20]

That is, in the general formula (13) [in the formula, V¹,
V², V³, V^Four, W¹, W², X², Y, m and n have the same meanings as above
Represents J^FourIs cyano, -C (O) NH₂, -C (O) NHCH₃Or-C (O) N
HCH₂CH ₂Represents CN, etc. ] The compound and general formula (1
4) [In the formula, J^FiveIs a sodium atom, trimethylsilyl or
Is a bird (C₁~ C_Four) Alkylstannyl (e.g., -Sn (Bu-
n)₃) Etc. ] The compound represented by
Known methods, such as the Journal of Heterocycle
K. Chemistry [J. Heterocyclic Chem.] 199
8 years, 35 volumes, 405 pages, Tetrahedron Letters
[Tetrahedron Lett.] 1991, 32, 6857.
Page, 1993, 34, 8011, 1997, 3
Volume 8, p. 1257, The Journal of Organics
Ku Chemistry [J. Org. Chem.] 1991, 56
Volume, 2395 pages, 1993, 58 volumes, 4139 pages.
Synthesis, 1996, p. 1428 and B.
Retin of the Chemical Society of
・ Japan [Bull. Chem. Soc. Jpn.] 1973, 4
React according to the method described in Volume 6, page 2176, etc.
Or the general formula (15) [wherein V¹, V², V³, V^Four,
W¹, W², X², Y, m and n have the same meanings as described above. ]so
The compound represented by the formula and sodium nitrite were
Methods of knowledge, eg, tetrahedron [Tetrahedron] 19
According to the method described in 1995, vol. 51, page 11737, etc.
By reacting, the compound of the general formula (2-3) [in the formula, V¹,
V², V³, V^Four, W¹, W², X², Y, m and n have the same meanings as above
Represents X¹Is X ¹-6 or X¹Represents -7. ] Compound represented by
Can be easily obtained.

Some of the compounds represented by the general formula (13) and the compounds represented by the general formula (15) used here are known compounds, and other compounds are the general compounds described in the literature. Can be synthesized from the compound represented by the general formula (10) described above.

(C). In the general formula (2), X ¹ is X ¹ -1, X ^1-
A general formula (2-4) represented by 8, X ¹ -9, X ¹ -10 or X ¹ -11 [wherein V ¹ , V ² , V ³ , V ⁴ , W ¹ , W ² , X ² , Y, m and n have the same meanings as described above. ] The manufacture of the compound represented by these.

[0104]

[Chemical 21]

General formula (16) [wherein V ¹ , V ² , V ³ , V ⁴ ,
W ¹ , W ² , X ² , Y, m and n have the same meanings as described above, and J ⁶ represents a halogen atom, —B (OH) ₂ or the like. And a compound represented by the general formula (17) [wherein, X ¹ is X ¹ -1, X ¹ -8, X ¹ -9, X ¹
-10 or X ¹ -11 is represented. ] Represented by a known method described in the literature, for example, Journal of the American Chemical Society [J. Am. Chem. Soc.]
1998, 120, 827, Journal of.
Heterocyclic chemistry [J. Heterocyclic
Chem.] 1977, 14, 1157, Tetrahedron Letters [Tetrahedron Lett.] 1996, 3
7, 299, 1998, 39, 2941 and 5617, Journal of Medicinal Chemistry [J. Med. Chem.] 1985, 28, 66.
Page, Synthetic Communications [Synth. C
ommun.] 1994, 24, 123 and 1995
Year 25, page 2165, etc., by reacting according to the general formula (2-4) [in the formula, V ¹ , V ² ,
V ³ , V ⁴ , W ¹ , W ² , X ² , Y, m and n have the same meanings as described above, and X ¹ is X ¹ -1, X ¹ -8, X ¹ -9, X ¹ -10. Or represents X ¹ -11. ]
A compound represented by can be obtained.

(D). Further, in the general formula (2) [in the formula, V ¹ , V ² ,
V ³ , V ⁴ , W ¹ , W ² , X ¹ , X ² , Y, m and n have the same meanings as described above. ] Another method for obtaining the compound represented by the following is the following method.

[0107]

[Chemical formula 22]

That is, the general formula (18) [wherein W ¹ ,
W ² , X ¹ , X ² and m have the same meanings as described above. ] And the compound represented by the general formula (7), wherein R ³ is a hydrogen atom (7-1) [wherein V ¹ , V ² , V ³ , V ⁴ , Y and n are the same as above] Express meaning. ] The compound represented by the above-mentioned, known methods described in the literature, for example, Journal of the Chemical Society Perkin Transactions,
1 [J. Chem. Soc. Perkin Trans. 1] 1994, 29
75 pages, Journal of the Chemical Society [J. Chem. Soc.] 1954, 2023, Berichte der Deutschen Hemischen Gesellschaft [Ber. Dtsch. Chem. Ges.] 1907, 40 volumes. Three
By reacting according to the method described on page 177 etc., the compound of the general formula (2) [in the formula, V ¹ , V ² , V ³ , V ⁴ , W ¹ , W ² ,
X ¹ , X ² , Y, m and n have the same meanings as described above. ] The compound represented by] can be easily synthesized.

Some of the compounds represented by the general formula (3) in the production methods A, C and E are known compounds, and some of them are commercially available. In addition, other compounds can also be synthesized according to the general synthetic method of the primary amine or secondary amine described in the literature.

Some of the compounds represented by the general formula (4) in the production method B are known compounds, and some of them are commercially available. In addition, other synthetic methods described in the literature, such as Chemistry Letters [Che
m. Lett.] 1976, p. 373, Tetrahedron Letters [Tetrahedron Lett.] 1972, 4339.
P., The Journal of Organic Chemistry [J. Org. Chem.] 1976, 41, 4028 and 1978, 43, 3244, Organic.
Synthesis [Org. Synth.] 1988, Collective Volume 6, page 101, Journal of the American Chemical Society [J. Am. Chem. So.
c.] 1964, 86, 4383, British patent (GB 2,
161,802), European patent (EP 0,051,273) and the like according to the method described therein.

In Production Method C, the compound represented by the general formula (5), which is a starting material compound for producing the compound of the present invention, can be synthesized as follows.

[0112]

[Chemical formula 23]

That is, the general formula (18) [wherein W ¹ ,
W ² , X ¹ , X ² and m have the same meanings as described above. And a compound represented by the general formula (7) [in the formula, V ¹ , V ² , V ³ , V ⁴ , Y,
R ³ and n have the same meanings as described above. ] By reacting with a compound represented by the same conditions as in the production method A,
General formula (5) [wherein V ¹ , V ² , V ³ , V ⁴ , W ² , X ¹ , X ² , Y,
R ³ , m and n have the same meanings as described above. ] The compound represented by these can be obtained.

In Production Method D, the compound represented by the general formula (6), which is a starting compound for producing the compound of the present invention, can be synthesized as follows.

[0115]

[Chemical formula 24]

That is, the general formula (18) [in the formula, W ¹ ,
W ² , X ¹ , X ² and m have the same meanings as described above. ] The compound represented by these, and general formula (3) [In formula, R < ¹ > and R < ² > represent the same meaning as the above. The compound represented by the formula] is reacted under the same conditions as in the production method A to give a compound of the general formula (6) [wherein W ¹ , X ¹ , X ² , R ¹ , R ² and m are the same as those defined above]. Have the same meaning. ] The compound represented by these can be obtained.

General formula (7) in production method D and production method F
Some of the compounds represented by are known compounds, and some of them are commercially available. Other than the above, general methods for synthesizing anilines described in the literature, such as The Journal of Organic Chemistry [J. Or.
g. Chem.] 1964, vol. 29, p. 1, Angevante.
Hemmy International Edition in English [Angew.Chem. Int. Ed. Engl.] 1985
Vol. 24, page 871, Synthesis 19
1984, 667 pages, Journal of the Chemical Society of Japan, 1973, 2351
P., German patent (DE 2606982), Japanese patent (JP-A-1-90163) and the like can be easily synthesized according to the method described therein.

In Production Method E, the compound represented by the general formula (8), which is a starting compound for producing the compound of the present invention, can be synthesized as follows.

[0119]

[Chemical 25]

That is, in the general formula (5), R ³ is a hydrogen atom (5-1) [wherein V ¹ , V ² , V ³ , V ⁴ , W
² , X ¹ , X ² , Y, m and n have the same meanings as described above. ] The compound represented by the formula is used in accordance with a general dehydration cyclization reaction described in the literature, for example, according to the method described in Journal of Medicinal Chemistry [J. Med. Chem.] 1967, 10: 982, etc. It can be easily synthesized by cyclization.

In Production Method F, the compound represented by the general formula (9), which is a starting material compound for producing the compound of the present invention, can be synthesized as follows.

[0122]

[Chemical formula 26]

That is, in the general formula (6), R ¹ is a hydrogen atom (6-1) [wherein, W ¹ , X ¹ , X ² , R ¹ and m have the same meanings as described above. ] The compound represented by
General cyclodehydration reactions described in the literature, such as Journal
Of Medicinal Chemistry [J. Med. Chem.]
It can be easily synthesized by cyclization according to the method described in 1967, vol. 10, page 982 and the like.

Some of the compounds represented by the general formula (11) and the compounds represented by the general formula (16) are known compounds, and other compounds are general synthetic methods described in the literature, For example, The Journal of Organic Chemistry [J. Org. Chem.] 1998, 63, 2
054, 1997, 62, 6458 and 199.
5 years, 60 volumes, 7508 pages, Tetrahedron Lett. 1997, 38 volumes, 3447
Page, and 1985, 26, 5997, Synthesis [Synthesis], 1994, 1146, and the like.

Some of the compounds represented by the general formula (12) and the compounds represented by the general formula (17) are known compounds, and some of them are commercially available. In addition, other compounds can be easily synthesized according to known synthesis methods described in the literature.

The compounds represented by the general formula (14) are known compounds, and some of them are commercially available. Also, other compounds can be easily synthesized by a known synthesis method described in the literature.

In the general formula (18), W ¹ and W ² are oxygen atoms, and the general formula (18-1) [wherein, X ¹ , X ² and m have the same meanings as described above. ] The compound represented by] can be synthesized as follows.

[0128]

[Chemical 27]

That is, in the general formula (19) [in the formula, X ¹ and X ²
And m have the same meanings as described above, and R represents lower alkyl such as methyl and ethyl. ] A compound represented by the general hydrolysis reaction described in the literature, for example, Journal of the American Chemical Society [J. Am. Che
m. Soc.] 1929, 51, 1865, Angevante Chemie [Angew. Chem.] 1951, 63, 329
According to the method described on page, etc., the general formula (20) [in the formula, X ¹ ,
X ² and m have the same meanings as described above. ], A general dehydration cyclization reaction described in the literature,
For example, by reacting under the conditions according to the method described in The Journal of Organic Chemistry [J. Org. Chem.] 1987, 52, 129, etc.,
A compound represented by the general formula (18-1) can be obtained.

Formula (19) [In the formula, X ¹ , X ² and m have the same meanings as described above, and R represents lower alkyl such as methyl and ethyl. ] The compound represented by] can be synthesized as follows.

[0131]

[Chemical 28]

That is, in the general formula (21) [wherein X ² and
m represents the same meaning as described above, and R represents lower alkyl such as methyl and ethyl. ] The compound represented by the general formula (2-
The reaction is conducted under the same conditions as in the production of the compound represented by 1), or by reacting the compound of the general formula (22) [wherein J ² , X ² and m have the same meanings as described above, and R is a lower group such as methyl or ethyl. Represents alkyl. And a compound represented by the general formula (12): [wherein J ³ has the same meaning as described above, X ¹ is X ¹ -2, X ¹ -3, X ¹ -6 or X ¹ -7.
Represents A compound represented by, general formula (2-2) represented by or be under the same conditions the reaction and production of the compound of the general formula (23) wherein, J ^4, X ² and m are the And R represents lower alkyl such as methyl and ethyl. ]
And a compound represented by the general formula (14) [wherein J ⁵ has the same meaning as described above. ] The compound represented by or general formula (2
4) [In the formula, X ² and m have the same meanings as described above, and R represents lower alkyl such as methyl and ethyl. ] The compound represented by the formula] and sodium nitrite are reacted under the same conditions as in the production of the compound represented by the formula (2-3), or the compound represented by the formula (25) [in the formula, J ⁶ , X ² and m have the same meaning as described above, and R represents lower alkyl such as methyl and ethyl. ]
And a compound represented by the general formula (17) [wherein, X ¹ is X ¹ -1,
Represents X ¹ -8, X ¹ -9, X ¹ -10 or X ¹ -11. ] The compound represented by the general formula (2-4) is reacted under the same conditions as in the production of the compound represented by the general formula (2-4) [wherein X ¹ , X ² and m are Has the same meaning as, R is methyl,
Represents lower alkyl such as ethyl. ] The compound represented by these can be obtained.

The compound represented by the general formula (21), the compound represented by the general formula (22), the compound represented by the general formula (23), the compound represented by the general formula (24) and the general formula ( 25) are known compounds (for example, The Journal of Organic Chemistry [J. Org. Chem.] 1987, 52, 129,
Journal of the American Chemical Society [J. Am. Chem. Soc.] 1929, 51, 18
Compounds described on page 65, etc. ), And other compounds can be easily synthesized using known methods described in the literature.

In each of these reactions, after completion of the reaction,
By carrying out the usual post-treatment, respective production intermediates which are the raw material compounds of the production methods AF can be obtained.

Each of the production intermediates produced by these methods can be directly used in the reaction of the next step without isolation and purification.

Specific examples of the compounds included in the present invention include the compounds shown in Tables 1 to 3. However, the compounds shown in Tables 1 to 3 are merely examples, and the present invention is not limited to these.

In the table, “Et” represents ethyl, and hereinafter, similarly, n-Pr and Pr-n are normal propyl, and i-Pr and Pr are the same.
-i is isopropyl, c-Pr and Pr-c are cyclopropyl, n-Bu and Bu-n are normal butyl, s-Bu and Bu-s are secondary butyl, and i-Bu and Bu-i are Isobutyl,
t-Bu and Bu-t are tertiary butyl, c-Bu and Bu-c are cyclobutyl, n-Pen and Pen-n are normal pentyl, c-Pen and Pen-c are cyclopentyl, and n-Hex And Hex
-n is normal hexyl, c-Hex and Hex-c represents cyclohexyl, Ph represents phenyl, Naph represents naphthyl, respectively, in the table T-1 ~ T-18, respectively represents the following structure,

[0138]

[Chemical 29]

The aromatic heterocycles represented by L-1a to L-48b in the table represent the following structures,

[0140]

[Chemical 30]

Further, the aliphatic heterocycles represented by M-4a to M-19a in the table have the following structures, respectively.

[0142]

[Chemical 31]

Further, in the table, the numbers representing the substitution positions of the substituent Y and the substituent Z respectively correspond to the positions of the numbers described in the structural formulas below. Table 1

[0144]

[Chemical 32]

[0145]

[Chemical 33]

[0146]

[Chemical 34]

[0147]

[Chemical 35]

[0148]

[Table 1] ――――――――――――――――――――――――――――――――――― R ¹ R ² R ³ (Y) _n ――――――――――――――――――――――――――――――――――― HHH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₃ HH 2-CH ₃ -4-OCHF ₂ CH ₃ HH 2-CH ₃ -4-OCF ₃ CH ₃ HH 2-CH ₃ -5-Cl CH ₃ CH ₃ H 2-CH ₃ -4-CF ₂ CF ₃ CH ₃ CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₃ CH ₃ H 2-CH ₃ -4-OCF ₃ CH ₃ CH ₃ CH ₃ 2-CH ₃ -4-CF ₂ CF ₃ Et HH 4-CF ₃ Et HH 2-F-4-CF ₂ CF ₃ Et HH 2-F-4-CF ₂ CF ₂ CF ₃ Et HH 2-Cl-4-CF ₂ CF ₃ Et HH 2-CH ₃ -4-CF ₂ CF ₃ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ Et HH 2-CH ₃ -4-OCHF ₂ Et HH 2-CH ₃ -4-OCF ₃ Et HH 2-CH ₃ -4-OCF ₂ CHF ₂ Et Et H 4-CF ₃ Et Et H 4-C (CF ₃ ) ₂ OH Et Et H 4-OCF ₃ Et Et H 4-SCF ₃ Et Et H 2-F-4-CF ₂ CF ₃ Et Et H 2-F-4-OCF ₃ Et Et H 2-Cl-4-CF ₂ CF ₃ Et Et H 2-CH ₃ -4-Cl Et Et H 2-CH ₃ -4-CF ₃ Et Et H 2-CH ₃ -4-CF ₂ CF ₃ Et Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et H 2-CH ₃ -4-OCHF ₂ Et Et H 2-CH ₃ -4-OCF ₃ Et Et H 2-CH ₃ -4-OCF ₂ CHF ₂ Et Et H 2-CH ₃ -4- (Ph-4-F) Et Et H 2-CH ₃ -4- (Ph-4-Cl) Et Et H 2-CH ₃ -4- (Ph-4-CF ₃ ) Et Et H 2-Et-4-CF ₂ CF ₃ Et Et H 2-Et-4-OCF ₃ Et Et H 3-OCF ₂ O-4 Et Et H 3-OCHFCF ₂ O-4 Et Et H 3-OCF ₂ CHFO-4 Et Et H 3-OC (CF ₂ CF ₃ ) = N-4 Et Et H 3-OC (Ph-2-CF ₃ ) = N-4 Et Et H 3-N = C (Ph-4-CF ₃ ) O-4 Et Et CH ₃ 2-CH ₃ -4-CF ₂ CF ₃ Et Et Et 2-CH ₃ -4-CF ₂ CF ₃ Et Et CH ₂ OCH ₃ 2-CH ₃ -4-CF ₂ CF ₃ Et Et CH ₂ OCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ OCH ₃ 2-CH ₃ -4-OCF ₃ Et Et CH ₂ OEt 2-CH ₃ -4-CF ₂ CF ₃ Et Et CH ₂ OEt 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ OEt 2-CH ₃ -4-OCF ₃ Et Et CH ₂ SCH ₃ 2-CH ₃ -4-CF ₂ CF ₃ Et Et CH ₂ SCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ SCH ₃ 2-CH ₃ -4-OCF ₃ Et Et CH ₂ SEt 2-CH ₃ -4-CF ₂ CF ₃ Et Et CH ₂ SEt 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ SEt 2-CH ₃ -4-OCF ₃ Et Et CH ₂ C (O) CH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ COOCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ COOEt 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ CN 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ CH = CH ₂ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CH ₂ C≡CH 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et C (O) CH ₃ 2-CH ₃ -4-CF ₂ CF ₃ Et Et C (O) CH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et C (O) CH ₃ 2-CH ₃ -4-OCF ₃ Et Et C (O) Et 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et C (O) Ph 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et C (O) OCH ₃ 2-CH ₃ -4-CF ₂ CF ₃ Et Et C (O) OCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et C (O) OCH ₃ 2-CH ₃ -4-OCF ₃ Et Et C (O) OEt 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et CN 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SCCl ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SPh 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Et) ₂ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Pr-i) ₂ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Bu-n) ₂ 2-CH ₃ -4-CF ₂ CF ₃ Et Et SN (Bu-n) ₂ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Bu-n) ₂ 2-CH ₃ -4-OCF ₃ Et Et S- (T-4) 2-CH ₃ -4-CF ₂ CF ₃ Et Et S- (T-4) 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et S- (T-4) 2-CH ₃ -4-OCF ₃ Et Et S- (T-1) 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et S- (T-2) 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et S- (T-3) 2-CH ₃ -4-CF ₂ CF ₃ Et Et S- (T-3) 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et S- (T-3) 2-CH ₃ -4-OCF ₃ Et Et SN (CH ₃ ) COOEt 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (CH ₃ ) COOPr-n 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (CH ₃ ) COOBu-n 2-CH ₃ -4-CF ₂ CF ₃ Et Et SN (CH ₃ ) COOBu-n 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (CH ₃ ) COOBu-n 2-CH ₃ -4-OCF ₃ Et Et SN (CH ₃ ) COOHex-n 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Et) COOEt 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Et) COOPr-n 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Et) COOBu-n 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Pr-i) COOEt 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Pr-i) COOPr-n 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et SN (Pr-i) COOBu-n 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et S (O) ₂ CH ₃ 2-CH ₃ -4-CF ₂ CF ₃ Et Et S (O) ₂ CH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et S (O) ₂ CH ₃ 2-CH ₃ -4-OCF ₃ Et Et S (O) ₂ Et 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et S (O) ₂ Ph 2-CH ₃ -4-CF (CF ₃ ) ₂ Et Et NHC (O) CH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ n-Pr HH 4-CF ₃ n-Pr HH 2-F-4-CF ₂ CF ₃ n-Pr HH 2-F-4-CF ₂ CF ₂ CF ₃ n-Pr HH 2-Cl-4-CF ₂ CF ₃ n-Pr HH 2-CH ₃ -3-Cl n-Pr HH 2-CH ₃ -4-CF ₂ CF ₃ n-Pr HH 2-CH ₃ -4-CF (CF ₃ ) ₂ n-Pr HH 2-CH ₃ -4-OCHF ₂ n-Pr HH 2-CH ₃ -4-OCF ₃ n-Pr HH 2-CH ₃ -4-OCF ₂ CHF ₂ n-Pr HH 2-OCH ₃ -5-Ph n-Pr CH ₃ H 2-CH ₃ -4-CF ₂ CF ₃ n-Pr Et H 4-OCHF ₂ n-Pr Et H 4-OCF ₃ n-Pr Et H 2-Cl-4-CF ₂ CF ₃ n-Pr Et H 2-CH ₃ -4-CF ₂ CF ₃ n-Pr Et H 2-CH ₃ -4-OCHF ₂ n-Pr Et H 2-CH ₃ -4-OCF ₃ n-Pr n-Pr H 2-CH ₃ -4-CF ₂ CF ₃ n-Pr n-Pr H 2-CH ₃ -4-OCHF ₂ n-Pr n-Pr H 2-CH ₃ -4-OCF ₃ n-Pr n-Pr H 2-CH ₃ -4-OCF ₂ CHF ₂ i-Pr HHH i-Pr HH 2-F i-Pr HH 2-Cl i-Pr HH 2-Br i-Pr HH 2-CH ₃ i-Pr HH 2-Et i-Pr HH 2-CF ₃ i-Pr HH 2-OCH ₃ i-Pr HH 2-SCH ₃ i-Pr HH 3-F i-Pr HH 3-Cl i-Pr HH 3-Br i-Pr HH 3-CH ₃ i-Pr HH 3-CF ₃ i-Pr HH 3-OCH ₃ i-Pr HH 3-OPr-i i-Pr HH 3-OCHF ₂ i-Pr HH 3-SCH ₃ i-Pr HH 3-SCF ₃ i-Pr HH 3-S (O) CF ₃ i-Pr HH 3- (L-10b) i-Pr HH 3- (L-13a) i-Pr HH 4-F i-Pr HH 4-Cl i-Pr HH 4-Br i-Pr HH 4-I i-Pr HH 4-CH ₃ i-Pr HH 4-Et i-Pr HH 4-Pr-n i-Pr HH 4-Pr-i i-Pr HH 4-Bu-n i-Pr HH 4-Bu-t i-Pr HH 4-CF ₃ i-Pr HH 4-CF ₂ CF ₃ i-Pr HH 4-CF ₂ CF ₂ CF ₃ i-Pr HH 4-CF (CF ₃ ) ₂ i-Pr HH 4-CF ₂ CF ₂ CF ₂ CF ₃ i-Pr HH 4-C (CF ₃ ) ₂ OH i-Pr HH 4-OCH ₃ i-Pr HH 4-OCHF ₂ i-Pr HH 4-OCF ₃ i-Pr HH 4-OCF ₂ CHFOCF ₃ i-Pr HH 4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ i-Pr HH 4-SCHF ₂ i-Pr HH 4-SCF ₃ i-Pr HH 4-SCF ₂ Br i-Pr HH 4-SCH ₂ CF ₃ i-Pr HH 4-SCF ₂ CHF ₂ i-Pr HH 4-SCF ₂ CF ₂ Br i-Pr HH 4-SCF ₂ CF ₂ CF ₃ i-Pr HH 4-SCF (CF ₃ ) ₂ i-Pr HH 4-SCF ₂ CF ₂ CF ₂ CF ₃ i-Pr HH 4-S (O) CF ₃ i-Pr HH 4-S (O) CF ₂ Br i-Pr HH 4-SO ₂ CF ₃ i-Pr HH 4-NO ₂ i-Pr HH 4-C (O) CH ₃ i-Pr HH 4-C (CH ₃ ) = NOCH ₃ i-Pr HH 4-C (CH ₃ ) = NOCH ₂ CH = CH ₂ i-Pr HH 4-CN i-Pr HH 4-CH = CCl ₂ i-Pr HH 4-CH = CBr ₂ i-Pr HH 4-CH = C (Cl) CF ₃ i-Pr HH 4-Ph i-Pr HH 4- (L-10b) i-Pr HH 2,4-F ₂ i-Pr HH 2-F-4-Cl i-Pr HH 2-F-4-CF ₂ CF ₃ i-Pr HH 2-F-4-CF ₂ CF ₂ CF ₃ i-Pr HH 2-F-4-CF (CF ₃ ) ₂ i-Pr HH 2-F-4-OCF ₃ i-Pr HH 2-F-4-O (Ph-2-Cl-4-CF ₃ ) i-Pr HH 2,5-F ₂ i-Pr HH 2,3-Cl ₂ i-Pr HH 2-Cl-4-F i-Pr HH 2,4-Cl ₂ i-Pr HH 2-Cl-4-CH ₃ i-Pr HH 2-Cl-4-CF ₃ i-Pr HH 2-Cl-4-CF ₂ CF ₃ i-Pr HH 2-Cl-4-CF ₂ CF ₂ CF ₃ i-Pr HH 2-Cl-4-CF (CF ₃ ) ₂ i-Pr HH 2-Cl-4-OCF ₃ i-Pr HH 2,5-Cl ₂ i-Pr HH 2,6-Cl ₂ i-Pr HH 2-Br-4-CF ₂ CF ₃ i-Pr HH 2-Br-4-CF (CF ₃ ) ₂ i-Pr HH 2-Br-4-OCF ₃ i-Pr HH 2-CH ₃ -3-F i-Pr HH 2-CH ₃ -3-Cl i-Pr HH 2,3- (CH ₃ ) ₂ i-Pr HH 2-CH ₃ -3-CF ₃ i-Pr HH 2-CH ₃ -3-OCH ₃ i-Pr HH 2-CH ₃ -3-OCHF ₂ i-Pr HH 2-CH ₃ -3-OCF ₂ CHFCl i-Pr HH 2-CH ₃ -4-F i-Pr HH 2-CH ₃ -4-Cl i-Pr HH 2-CH ₃ -4-Br i-Pr HH 2-CH ₃ -4-I i-Pr HH 2,4- (CH ₃ ) ₂ i-Pr HH 2-CH ₃ -4-CH ₂ CH ₂ Bu-t i-Pr HH 2-CH ₃ -4-CF ₃ i-Pr HH 2-CH ₃ -4-CF ₂ CF ₃ i-Pr HH 2-CH ₃ -4-CF ₂ CF ₂ CF ₃ i-Pr HH 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr HH 2-CH ₃ -4-CF ₂ CF ₂ CF ₂ CF ₃ i-Pr HH 2-CH ₃ -4-CF (CF ₃ ) CF ₂ CF ₃ i-Pr HH 2-CH ₃ -4-CF ₂ (CF ₂ ) _Four CF ₃ i-Pr HH 2-CH ₃ -4-OCH ₃ i-Pr HH 2-CH ₃ -4-OPr-i i-Pr HH 2-CH ₃ -4-OCHF ₂ i-Pr HH 2-CH ₃ -4-OCF ₃ i-Pr HH 2-CH ₃ -4-OCF ₂ Br i-Pr HH 2-CH ₃ -4-OCH ₂ CF ₃ i-Pr HH 2-CH ₃ -4-OCF ₂ CHF ₂ i-Pr HH 2-CH ₃ -4-OCF ₂ CHFCl i-Pr HH 2-CH ₃ -4-OCF ₂ CF ₂ Br i-Pr HH 2-CH ₃ -4-OCF ₂ CFCl ₂ i-Pr HH 2-CH ₃ -4-OCF ₂ CCl ₃ i-Pr HH 2-CH ₃ -4-OCH ₂ CF ₂ CHF ₂ i-Pr HH 2-CH ₃ -4-OCF ₂ CHFCF ₃ i-Pr HH 2-CH ₃ -4-OCF ₂ CFBrCF ₃ i-Pr HH 2-CH ₃ -4-OCF ₂ CHFOCF ₃ i-Pr HH 2-CH ₃ -4-OCF ₂ CF ₂ Ph i-Pr HH 2-CH ₃ -4-OCH ₂ OCH ₃ i-Pr HH 2-CH ₃ -4-OCH ₂ SCH ₃ i-Pr HH 2-CH ₃ -4-OC (CF ₂ CF ₃ ) = C (CF ₃ ) ₂ i-Pr HH 2-CH ₃ -4-OC (OCH ₃ ) = C (CF ₃ ) ₂ i-Pr HH 2-CH ₃ -4-O (Ph-3-CF ₃ ) i-Pr HH 2-CH ₃ -4-O (Ph-2-Cl-4-CF ₃ ) i-Pr HH 2-CH ₃ -4-OC ₆ F _Five i-Pr HH 2-CH ₃ -4-O (L-45c) i-Pr HH 2-CH ₃ -4-O (L-45d) i-Pr HH 2-CH ₃ -4-O (L-48a) i-Pr HH 2-CH ₃ -4-O (L-48b) i-Pr HH 2-CH ₃ -4-OP (S) (OCH ₃ ) ₂ i-Pr HH 2-CH ₃ -4-SCH ₃ i-Pr HH 2-CH ₃ -4-SPr-i i-Pr HH 2-CH ₃ -4-SCHF ₂ i-Pr HH 2-CH ₃ -4-SCF ₂ CF ₃ i-Pr HH 2-CH ₃ -4-SCF ₂ CF ₂ CF ₃ i-Pr HH 2-CH ₃ -4-SCH ₂ CH ₂ CF = CF ₂ i-Pr HH 2-CH ₃ -4-S (Ph-4-Cl) i-Pr HH 2-CH ₃ -4-S (O) CF ₃ i-Pr HH 2-CH ₃ -4-S (O) CH ₂ CH ₂ CF = CF ₂ i-Pr HH 2-CH ₃ -4-SO ₂ CH ₂ CH ₂ CF = CF ₂ i-Pr HH 2-CH ₃ -4-NO ₂ i-Pr HH 2-CH ₃ -4-C (O) CF ₃ i-Pr HH 2-CH ₃ -4-C (CH ₃ ) = NOCH ₃ i-Pr HH 2-CH ₃ -4-C (O) OCH ₃ i-Pr HH 2-CH ₃ -4-C (O) OCH ₂ CF ₃ i-Pr HH 2-CH ₃ -4-CN i-Pr HH 2-CH ₃ -4-C≡C Bu-t i-Pr HH 2-CH ₃ -4-C≡CPh i-Pr HH 2-CH ₃ -4-C≡C (Ph-2,4-Cl ₂ ) i-Pr HH 2-CH ₃ -4- (Ph-4-CF ₃ ) i-Pr HH 2-CH ₃ -4- (Ph-4-OCF ₃ ) i-Pr HH 2-CH ₃ -4- (L-10a) i-Pr HH 2-CH ₃ -4-P (O) (OEt) ₂ i-Pr HH 2-CH ₃ -5-F i-Pr HH 2-CH ₃ -5-Cl i-Pr HH 2-CH ₃ -5-Br i-Pr HH 2,5- (CH ₃ ) ₂ i-Pr HH 2-CH ₃ -5- (L-10a) i-Pr HH 2-CH ₃ -6-Cl i-Pr HH 2,6- (CH ₃ ) ₂ i-Pr HH 2-Et-4-Cl i-Pr HH 2-Et-4-I i-Pr HH 2-Et-4-CF ₂ CF ₃ i-Pr HH 2-Et-4-CF (CF ₃ ) ₂ i-Pr HH 2-Et-4-OCF ₃ i-Pr HH 2-Et-5-F i-Pr HH 2,6- (Et) ₂ i-Pr HH 2- (Pr-n) -4-I i-Pr HH 2- (Pr-i) -4-I i-Pr HH 2- (Pr-i) -4-CF (CF ₃ ) ₂ i-Pr HH 2- (Bu-n) -4-I i-Pr HH 2-CF ₃ -4-Cl i-Pr HH 2-CF ₃ -4-CF ₂ CF ₃ i-Pr HH 2-CF ₃ -4-OCHF ₂ i-Pr HH 2-CF ₂ CF ₃ -4-Br i-Pr HH 2,4- (CF ₂ CF ₃ ) ₂ i-Pr HH 2-OCF ₂ O-3 i-Pr HH 2-OCH ₃ -4-CF ₂ CF ₃ i-Pr HH 2-OCH ₃ -4-CF (CF ₃ ) ₂ i-Pr HH 2-OCH ₃ -5-Ph i-Pr HH 2-OEt-4-CF (CF ₃ ) ₂ i-Pr HH 2-OPh-4-CF (CF ₃ ) ₂ i-Pr HH 2-SCH ₃ -4-CF ₂ CF ₃ i-Pr HH 2-SCH ₃ -4-CF (CF ₃ ) ₂ i-Pr HH 2-Ph-4-CF (CF ₃ ) ₂ i-Pr HH 3,4-F ₂ i-Pr HH 3-F-4-CF (CF ₃ ) ₂ i-Pr HH 3-F-4-OCHF ₂ i-Pr HH 3-Cl-4-F i-Pr HH 3,4-Cl ₂ i-Pr HH 3-Cl-4-CF ₂ CF ₃ i-Pr HH 3-Cl-4-CF (CF ₃ ) ₂ i-Pr HH 3-Cl-4-OCHF ₂ i-Pr HH 3,5-Cl ₂ i-Pr HH 3-CH ₃ -4-Br i-Pr HH 3-CH ₃ -4-CF ₂ CF ₃ i-Pr HH 3-CF ₃ -4-Cl i-Pr HH 3-CF ₃ -4-OCHF ₂ i-Pr HH 3-CF ₃ -5-OCH ₃ i-Pr HH 3-OCH ₃ -4-OCHF ₂ i-Pr HH 3,4- (OCHF ₂ ) ₂ i-Pr HH 3-SCH ₃ -4-CF (CF ₃ ) ₂ i-Pr HH 3-OCH ₂ O-4 i-Pr HH 3-OCF ₂ O-4 i-Pr HH 3-OCF ₂ CF ₂ -4 i-Pr HH 3-OCHFCF ₂ O-4 i-Pr HH 3-OCF ₂ CHFO-4 i-Pr HH 3-OCF ₂ CF ₂ O-4 i-Pr HH 3-OCF ₂ OCF ₂ -4 i-Pr HH 3-OC (CF ₂ CF ₃ ) = N-4 i-Pr HH 3-OC (CF ₂ CF ₂ CF ₃ ) = N-4 i-Pr HH 3-SC (Pr-i) = N-4 i-Pr HH 3-N = C (CF ₃ ) O-4 i-Pr HH 3-N = C (CF ₂ CF ₃ ) O-4 i-Pr HH 3-N = C (CF ₂ CF ₂ CF ₃ ) O-4 i-Pr HH 3-N = C (Ph-4-CF ₃ ) O-4 i-Pr HH 3-N = C (CF ₃ ) NH-4 i-Pr HH 3-N = C (CF ₃ ) N (CH ₃ ) -4 i-Pr HH 2,3,4-F ₃ i-Pr HH 2-F-4-OCF ₂ O-5 i-Pr HH 2,3,4-Cl ₃ i-Pr HH 2,6-Cl ₂ -4-CF ₃ i-Pr HH 2-Cl-3-OCHFCF ₂ O-4 i-Pr HH 2-Cl-3-OCF ₂ CHFO-4 i-Pr HH 2-Cl-3-OCF ₂ CF ₂ O-4 i-Pr HH 2-Cl-3-N = C (CF ₃ ) O-4 i-Pr HH 2-Cl-4-OCF ₂ O-5 i-Pr HH 2-Cl-4-OCHFCF ₂ O-5 i-Pr HH 2-Cl-4-OCF ₂ CHFO-5 i-Pr HH 2-Cl-4-OCF ₂ CF ₂ O-5 i-Pr HH 2-Br-4-CF (CF ₃ ) ₂ -5-CH ₃ i-Pr HH 2-Br-4-OCF ₂ CHFO-5 i-Pr HH 2-I-4-OCF ₂ O-5 i-Pr HH 2,4- (CH ₃ ) ₂ -3-Cl i-Pr HH 2-CH ₃ -3-Cl-4-OCHF ₂ i-Pr HH 2,3- (CH ₃ ) ₂ -4-Cl i-Pr HH 2,3- (CH ₃ ) ₂ -4-Br i-Pr HH 2,3- (CH ₃ ) ₂ -4-CF ₂ CF ₃ i-Pr HH 2,3- (CH ₃ ) ₂ -4-CF (CF ₃ ) ₂ i-Pr HH 2,3- (CH ₃ ) ₂ -4-OCH ₃ i-Pr HH 2,3- (CH ₃ ) ₂ -4-SCH ₃ i-Pr HH 2,3- (CH ₃ ) ₂ -4-NO ₂ i-Pr HH 2,4- (CH ₃ ) ₂ -3-OCH ₃ i-Pr HH 2,4- (CH ₃ ) ₂ -3-OCHF ₂ i-Pr HH 2-CH ₃ -4,5-Cl ₂ i-Pr HH 2-CH ₃ -4-CF ₂ CF ₃ -5-Cl i-Pr HH 2-CH ₃ -4-CF ₂ CF ₃ -5-CH ₃ i-Pr HH 2-CH ₃ -4-CF (CF ₃ ) ₂ -5-F i-Pr HH 2-CH ₃ -4-CF (CF ₃ ) ₂ -5-Cl i-Pr HH 2-CH ₃ -4-OCHF ₂ -5-Cl i-Pr HH 2-CH ₃ -4-OCF ₂ CHF ₂ -5-Cl i-Pr HH 2-CH ₃ -4-CF ₂ CF ₂ O-5 i-Pr HH 2-CH ₃ -4-OCF ₂ O-5 i-Pr HH 2-CH ₃ -4-OCHFCF ₂ O-5 i-Pr HH 2-CH ₃ -4-OC (CF ₃ ) = N-5 i-Pr HH 2,4,6- (CH ₃ ) ₃ i-Pr HH 2,6- (CH ₃ ) ₂ -4-CF ₂ CF ₃ i-Pr HH 2,6- (CH ₃ ) ₂ -4-CF (CF ₃ ) ₂ i-Pr HH 2,6- (Et) ₂ -3-Cl i-Pr HH 2- (CH ₂ ) _Four -3-4-CF (CF ₃ ) ₂ i-Pr HH 2-OCF ₂ O-3-6-Cl i-Pr HH 2-N = CHS-3-4-CF (CF ₃ ) ₂ i-Pr HH 3,5-Cl ₂ -4-OCHF ₂ i-Pr HH 2,5-Cl ₂ -3-OCHFCF ₂ O-4 i-Pr HH 2,6-Cl ₂ -3-OCHFCF ₂ O-4 i-Pr HH 2,3-Br ₂ -4-OCHFCF ₂ O-5 i-Pr HH 2,3-Br ₂ -4-OCF ₂ CHFO-5 i-Pr HH 2,5-Br ₂ -3-OCHFCF ₂ O-4 i-Pr HH 2,5-Br ₂ -3-OCF ₂ CHFO-4 i-Pr HH 2,6-Br ₂ -3-OCHFCF ₂ O-4 i-Pr HH 2,6-Br ₂ -3-OCF ₂ CHFO-4 i-Pr HH 2,3,4,5,6-F _Five i-Pr H CH ₃ 2-CH ₃ -4-Cl i-Pr CH ₃ H 4-CF ₃ i-Pr CH ₃ H 2-CH ₃ -4-Cl i-Pr CH ₃ H 2-CH ₃ -4-CF ₂ CF ₃ i-Pr CH ₃ H 2-CH ₃ -4-OCHF ₂ i-Pr CH ₃ CH ₃ 2-CH ₃ -4-CF ₂ CF ₃ i-Pr Et H 4-OCF ₃ i-Pr Et H 2-CH ₃ -4-CF ₂ CF ₃ i-Pr i-Pr H 2-CH ₃ -4-CF ₂ CF ₃ i-Pr C (O) CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr C (O) Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr C (O) Ph H 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr C (O) OCH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr C (O) OEt H 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr SN (Bu-n) ₂ H 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr S (O) ₂ CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Pr NHC (O) CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ c-Pr HH 4-CF ₃ c-Pr HH 2-CH ₃ -4-CF ₂ CF ₃ c-Pr HH 2-CH ₃ -4-CF (CF ₃ ) ₂ c-Pr HH 2-CH ₃ -4-OCHF ₂ c-Pr HH 2-CH ₃ -4-OCF ₃ c-Pr HH 2-CH ₃ -5-Cl n-Bu HH 2-CH ₃ -4-CF ₂ CF ₃ n-Bu HH 2-CH ₃ -4-CF (CF ₃ ) ₂ n-Bu HH 2-CH ₃ -4-OCF ₃ i-Bu HH 4-CF ₃ i-Bu HH 2-CH ₃ -4-CF ₂ CF ₃ i-Bu HH 2-CH ₃ -4-CF (CF ₃ ) ₂ i-Bu HH 2-CH ₃ -4-OCHF ₂ i-Bu HH 2-CH ₃ -4-OCF ₃ i-Bu CH ₃ H 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ Pr-c HH 2-CH ₃ -5-F CH ₂ Pr-c HH 2-CH ₃ -4-CF (CF ₃ ) ₂ s-Bu HH 4-CF ₃ s-Bu HH 2-F-4-CF ₂ CF ₃ s-Bu HH 2-F-4-CF ₂ CF ₂ CF ₃ s-Bu HH 2-Cl-4-CF ₂ CF ₃ s-Bu HH 2-CH ₃ -4-CF ₂ CF ₃ s-Bu HH 2-CH ₃ -4-CF (CF ₃ ) ₂ s-Bu HH 2-CH ₃ -4-OCHF ₂ s-Bu HH 2-CH ₃ -4-OCF ₃ s-Bu HH 2-CH ₃ -5-Cl s-Bu HH 2-Et-4-CF ₂ CF ₃ t-Bu HHH t-Bu HH 4-CF ₃ t-Bu HH 4-CF ₂ CF ₃ t-Bu HH 4-C (CF ₃ ) ₂ OH t-Bu HH 4-OCF ₃ t-Bu HH 4-SCF ₃ t-Bu HH 4-SCF ₂ Br t-Bu HH 4-SO ₂ CF ₃ t-Bu HH 2-F-4-CF ₂ CF ₃ t-Bu HH 2-F-4-CF ₂ CF ₂ CF ₃ t-Bu HH 2-F-4-CF (CF ₃ ) ₂ t-Bu HH 2-F-4-OCF ₃ t-Bu HH 2-Cl-4-CF ₂ CF ₃ t-Bu HH 2-Cl-4-CF (CF ₃ ) ₂ t-Bu HH 2-Cl-4-OCF ₃ t-Bu HH 2-Br-4-CF ₂ CF ₃ t-Bu HH 2-CH ₃ -4-Cl t-Bu HH 2-CH ₃ -4-CF ₃ t-Bu HH 2-CH ₃ -4-CF ₂ CF ₃ t-Bu HH 2-CH ₃ -4-CF (CF ₃ ) ₂ t-Bu HH 2-CH ₃ -4-OCHF ₂ t-Bu HH 2-CH ₃ -4-OCF ₃ t-Bu HH 2-CH ₃ -4-OCF ₂ Br t-Bu HH 2-CH ₃ -4-OCF ₂ CHF ₂ t-Bu HH 2-CH ₃ -4-S (O) CF ₃ t-Bu HH 2-CH ₃ -5-Cl t-Bu HH 2-Et-4-CF ₂ CF ₃ t-Bu HH 2-Et-4-CF (CF ₃ ) ₂ t-Bu HH 2-Et-4-OCF ₃ t-Bu HH 2- (Pr-i) -4-CF (CF ₃ ) ₂ t-Bu HH 2-CF ₃ -4-CF ₂ CF ₃ t-Bu HH 2-OCH ₃ -4-CF ₂ CF ₃ t-Bu HH 2-OEt-4-CF (CF ₃ ) ₂ t-Bu HH 2-SCH ₃ -4-CF (CF ₃ ) ₂ t-Bu HH 3-F-4-CF (CF ₃ ) ₂ t-Bu HH 3-Cl-4-CF ₂ CF ₃ t-Bu HH 3-OCF ₂ O-4 t-Bu HH 3-OCHFCF ₂ O-4 t-Bu HH 3-OCF ₂ CHFO-4 t-Bu HH 3-OCF ₂ CF ₂ O-4 t-Bu HH 3-OC (CF ₂ CF ₃ ) = N-4 t-Bu HH 3-N = C (CF ₂ CF ₃ ) O-4 t-Bu HH 3-N = C (CF ₂ CF ₂ CF ₃ ) O-4 t-Bu HH 3-N = C (Ph-4-CF ₃ ) O-4 t-Bu HH 2-F-4-OCF ₂ O-5 t-Bu HH 2-Cl-3-OCF ₂ CF ₂ O-4 t-Bu HH 2-Cl-3-N = C (CF ₃ ) O-4 t-Bu HH 2-Cl-4-OCF ₂ O-5 t-Bu HH 2-Cl-4-OCF ₂ CF ₂ O-5 t-Bu HH 2,3- (CH ₃ ) ₂ -4-CF ₂ CF ₃ t-Bu HH 2,3- (CH ₃ ) ₂ -4-CF (CF ₃ ) ₂ t-Bu HH 2-CH ₃ -4-CF ₂ CF ₃ -5-Cl t-Bu HH 2-CH ₃ -4-CF ₂ CF ₃ -5-CH ₃ t-Bu HH 2-CH ₃ -4-CF (CF ₃ ) ₂ -5-F t-Bu HH 2-CH ₃ -4-OCHFCF ₂ O-5 t-Bu HH 2- (CH ₂ ) _Four -3-4-CF (CF ₃ ) ₂ t-Bu HH 2-OCF ₂ O-3-4-Cl t-Bu HH 2-OCF ₂ O-3-4,6-Cl ₂ t-Bu H CH ₃ 4-OCF ₃ c-Bu HH 2-CH ₃ -4-CF (CF ₃ ) ₂ c-Bu HH 2-CH ₃ -5-F c-Bu HH 2-CH ₃ -5-Cl n-Pen HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH (CH ₃ ) Et HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Et) ₂ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Et) ₂ HH 2-CH ₃ -4-OCHF ₂ CH (CH ₃ ) Pr-n HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) Pr-i HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) Pr-i HH 2-CH ₃ -4-OCHF ₂ C (CH ₃ ) ₂ Et HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ Et HH 2-CH ₃ -4-OCHF ₂ C (CH ₃ ) ₂ Et HH 2-CH ₃ -4-OCF ₃ CH ₂ CH ₂ Pr-i HH 2-CH ₃ -4-CF ₂ CF ₃ c-Pen HH 2-CH ₃ -4-CF ₂ CF ₃ c-Pen HH 2-CH ₃ -4-OCHF ₂ c-Pen HH 2-CH ₃ -5-Cl n-Hex HH 2-CH ₃ -4-CF ₂ CF ₃ c-Hex HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ Hex-c HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ FHH 2-CH ₃ -4-OCHF ₂ CH ₂ CH ₂ FHH 2-CH ₃ -5-F CH ₂ CH ₂ Cl HH 2-CH ₃ -5-F CH ₂ CF ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CF ₃ HH 2-CH ₃ -5-Cl (S) -CH (CH ₃ ) CH ₂ FHH 2-CH ₃ -4-CF ₂ CF ₃ (R) -CH (CH ₃ ) CH ₂ Br HH 2-CH ₃ -4-CF ₂ CF ₃ (S) -CH (CH ₃ ) CH ₂ Br HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ Cl HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ Cl HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH ₂ Br HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ Br HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CHBrCH ₂ Br HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ OCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ OCH ₃ HH 2-CH ₃ -4-OCHF ₂ CH ₂ CH ₂ OCH ₃ HH 2-CH ₃ -5-Cl CH ₂ CH ₂ OEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ OEt CH ₂ CH ₂ OEt H 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH (OH) CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH (OH) Et HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH (OH) Ph HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH (OH) CH ₂ Ph HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ (R) -CH (CH ₃ ) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ (S) -CH (CH ₃ ) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ OCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ OCH ₃ HH 2-CH ₃ -4-OCHF ₂ CH (Et) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Et) CH ₂ OCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Ph) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ (R) -CH (Ph) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Ph-2-Cl) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Ph-4-Cl) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Ph-4-Ph) CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ OH HH 2-CH ₃ -4-OCF ₃ CH ₂ CH (OEt) ₂ HH 2-CH ₃ -4-OCHF ₂ CH ₂ CH ₂ CH ₂ OH HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ CH ₂ OCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ SCH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ SCH ₃ Et H 2-CH ₃ -4-OCF ₃ CH ₂ SCH ₃ Et H 2-CH ₃ -4-OCF ₂ CF ₃ CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₃ CH ₂ CH ₂ SCH ₃ CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SCH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SCH ₃ Pr-n H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ S (O) CH ₃ CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ S (O) CH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SO ₂ CH ₃ CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SO ₂ CH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SEt HH 2-CH ₃ -4-OCF ₃ CH ₂ CH ₂ SPr-i HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ SPr-i HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ SPr-i HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SH HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 4-OCF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Cl-4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Cl-4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Cl-4-OCF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -3-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-Cl CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ (R) -CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ (S) -CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-OCHF ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₂ CHFCF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-OC (CF ₂ CF ₃ ) = C (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-O (L-45d) CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-SCF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-Si (CH ₃ ) ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -5-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Et-4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Et-4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-OCH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Cl-4-OCHFCF ₂ O-5 CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Cl-4-OCF ₂ CHFO-5 CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ -5-F CH (CH ₃ ) CH ₂ SCH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-Cl-4-OCF ₃ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF ₃ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₃ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-O (L-45d) CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-Cl-4-OCF ₃ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-Cl-4-OCHFCF ₂ O-5 CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-Cl-4-OCF ₂ CHFO-5 CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF ₃ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₃ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-O (L-45d) CH (CH ₃ ) CH ₂ SEt HH 2-CH ₃ -4-Cl CH (CH ₃ ) CH ₂ SEt HH 2-CH ₃ -4-CF ₃ CH (CH ₃ ) CH ₂ SEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ (S) -CH (CH ₃ ) CH ₂ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SEt HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ S (O) Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SPr-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SPr-i HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SPr-i HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SBu-n HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SBu-n HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SBu-i HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SBu-i HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SBu-i HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SBu-t HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SBu-t HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SBu-t HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SO ₂ Bu-t HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SHex-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SHex-n HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SHex-c HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SHex-c HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SCH ₂ CF ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) CH ₂ CF ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ CH ₂ CF ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ OH HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ OCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) CH ₂ CH ₂ OCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ CH ₂ CH ₂ OCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) CH ₂ CH ₂ OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ CH ₂ CH ₂ OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ OC (O) CF ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SCH ₂ CH = CH ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ C≡CH HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SC (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ C (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ CH ₂ C (O) OCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SC (O) NHEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SC (O) N (CH ₃ ) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SC (O) N (Et) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SC (S) NHCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SC (S) NHEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SC (S) N (CH ₃ ) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ C (O) N (Et) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) CH ₂ C (O) N (Et) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ CH ₂ C (O) N (Et) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₂ (Ph-2,4-Cl ₂ ) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SPh HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SPh HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SPh HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ SPh HH 2-Et-4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ S (L-8a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ (L-8a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (L-36a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (L-45a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ S (L-45a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (L-45a) HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ S (O) (L-45a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ S (O) (L-45a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ (L-45a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SO ₂ (L-45a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ (L-45a) HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ S (L-48c) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) (L-48c) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ (L-48c) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SSCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SS (Ph-2-NO ₂ ) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (Et) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₂ SCH ₃ ) ₂ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₂ SCH ₃ ) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (Ph) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (Ph) CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (Ph) CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH (CH ₃ ) SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH (CH ₃ ) SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH (CH ₃ ) SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH (CH ₃ ) SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 4-SO ₂ N (Et) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2,4-Cl ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-Cl-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-Cl-4-OCF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-Br C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-C (CF ₃ ) ₂ OH C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-C (CF ₃ ) ₂ OCH ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-C (CF ₃ ) ₂ OCH ₂ Ph C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-OSO ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4- (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CH ₂ (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CH (OH) (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-C (O) (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-C (O) N (CH ₃ ) (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-C (= NOH) (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-C (= NOCH ₃ ) (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-O (Ph-3-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-O (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-O (Ph-3-CN) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-O (L-45d) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-S (Ph-3-Cl) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-Et-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₂ OH-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 3-CF ₂ OCF ₂ O-4 C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-Cl-3-CF ₂ OCF ₂ O-4 C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -3-F-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-Cl-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-Cl-4-OCF ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ (-)-C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ (+)-C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-C (CF ₃ ) ₂ OCH ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-OSO ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-O (L-45d) C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-Et-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -3-F-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-Cl-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-Cl-4-OCF ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-C (CF ₃ ) ₂ OCH ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4- (Ph-4-Cl) C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-O (L-45d) C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-Et-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -3-F-4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SEt HH 2-Cl-4-OCF ₃ C (CH ₃ ) ₂ CH ₂ SEt HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) Et HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ S (O) Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ Et HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ Et HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH ₂ SPr-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) Pr-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ Pr-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SPr-i HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SPr-i HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) Pr-i HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ Pr-i HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SBu-t HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) Bu-t HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SPh HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) Ph HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ Ph HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₂ (Ph-4-Cl) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (L-45a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) (L-45a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ (L-45a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH (CH ₃ ) SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH (CH ₃ ) SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH (CH ₃ ) SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH (CH ₃ ) SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₃ CH ₂ CH ₂ CH ₂ SCH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ CH ₂ S (O) CH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ CH ₂ SO ₂ CH ₃ Et H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ CH ₂ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ CH ₂ S (O) Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ CH ₂ SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (Et) CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₂ OH) CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ CH ₂ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ CH ₂ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) ₃ SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) ₃ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) ₃ SCH ₃ HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) (CH ₂ ) ₃ S (O) CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) ₃ S (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) ₃ SO ₂ CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) ₃ SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) ₃ SEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) ₃ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) ₃ S (O) Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) ₃ SO ₂ Et HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) ₃ SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ (CH ₂ ) ₃ SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ (CH ₂ ) ₃ SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ (CH ₂ ) ₃ SEt HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH ₂ CH ₂ CH (CH ₃ ) SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) _Four SCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) _Four SCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) _Four SO ₂ CH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) _Four SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) _Four SEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) _Four SEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) _Four S (O) Et HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) _Four S (O) Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) (CH ₂ ) _Four SO ₂ Et HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (CH ₂ ) _Four SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-5 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-6 HH 2-CH ₃ -4-CF ₂ CF ₃ T-6 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-7 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-8 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-9 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-10 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-11 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-12 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-13 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-14 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-15 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ T-16 HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ NHC (O) OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-Cl C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-CF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-OCF ₂ CHFCF ₃ C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CHO HH 2-CH ₃ -4-O (L-45d) CH (CHO) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) (CHO) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) (CHO) CH ₂ SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH = NOCH ₃ CH ₃ H 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH = NOCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH = NOCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH = NOCH ₃ HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH = NOPr-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH = NOCH ₂ Pr-c HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH = NOCH ₂ CH ₂ OEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH = NOCH ₂ CH ₂ SEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH = NOCH ₂ CH = CH ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH = NOCH ₂ Ph HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOH HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOH HH 2-CH ₃ -4-OCF ₂ CF ₃ C (CH ₃ ) ₂ CH = NOH HH 2-CH ₃ -4-OCF ₂ CHFCF ₃ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-Cl-4-CF ₃ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-Cl C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-CF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-OCHF ₂ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-OCF ₂ CHF ₂ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-OCF ₂ CHFCF ₃ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -4-O (L-45d) C (CH ₃ ) ₂ CH = NOEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOCH ₂ C (O) OBu-t HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH = NOCH ₂ C (O) N (Et) ₂ HH 2-CH ₃ -4-OCF ₃ CH ₂ CH ₂ CH = NOCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ CH ₂ CH = NOEt HH 2-CH ₃ -4-OCF ₃ CH (CH ₃ ) CH ₂ CH = NOCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (CH ₃ ) = NOCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ C (Ph) = NOCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) (CH = NOH) CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) (CH = NOH) CH ₂ SO ₂ Et HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ C (O) OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ C (O) OEt HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ C (O) OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ C (O) OEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) NHEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) NHPr-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) NHBu-n HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) NHCH ₂ Ph HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) N (CH ₃ ) ₂ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) C (O) N (CH ₃ ) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) N (Et) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O) N (Pr-n) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O)-(T-4) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O)-(T-17) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) C (O)-(T-18) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ C (O) NHCH ₃ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ C (O) NHEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ C (O) N (CH ₃ ) ₂ HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) CH ₂ C (O) N (CH ₃ ) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ C (O) N (Et) ₂ HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ C (O) N (CH ₃ ) Ph HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = CHC (O) NHEt HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH = CH ₂ HH 4-CF ₃ CH ₂ CH = CH ₂ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH = CH ₂ HH 2-CH ₃ -4-OCHF ₂ CH ₂ CH = CH ₂ CH ₂ CH = CH ₂ H 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH = CH ₂ HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ CH = CHPh (E) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ CH = CF ₂ HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ C≡CH HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ C≡CH HH 2-CH ₃ -4-OCHF ₂ CH ₂ C≡CH HH 2-CH ₃ -5-Cl C (CH ₃ ) ₂ C≡CH HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡CH HH 2-CH ₃ -4-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ C≡CH HH 2-CH ₃ -4-OCHF ₂ C (CH ₃ ) ₂ C≡CH HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ C≡CPh HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C (Ph-4-CH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C (Ph-4-CF ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C (Ph-4-OCH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C (Ph-4-OCF ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C (Ph-2,4-F ₂ ) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C (Ph-2,4-Cl ₂ ) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C (Ph-2,6-Cl ₂ ) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C Naph HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C- (L-1a) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C- (L-2a) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C- (L-45a) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C- (L-45b) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ C≡C- (L-46a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ Ph HH 2-F-4-CF ₂ CF ₃ CH ₂ Ph HH 2-Cl-4-CF ₂ CF ₃ CH ₂ Ph HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ Ph HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ Ph HH 2-CH ₃ -4-OCHF ₂ CH ₂ Ph HH 2-CH ₃ -4-OCF ₃ CH ₂ Ph CH ₃ H 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ Ph CH ₃ H 2-CH ₃ -4-OCHF ₂ CH ₂ Ph CH ₃ CH ₃ 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ Ph Et H 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-F) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-F) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ (Ph-2-F) CH ₃ H 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-Cl) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ (Ph-2-Cl) HH 2-CH ₃ -4-OCHF ₂ CH ₂ (Ph-2-Cl) HH 2-CH ₃ -4-OCF ₃ CH ₂ (Ph-3-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-3-Cl) CH ₃ H 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-4-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-CH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-CH ₃ ) HH 2-CH ₃ -4-OCHF ₂ CH ₂ (Ph-3-CH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-4-CH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-OCH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-3-OCH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-4-OCH ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2-CF ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-4-OCF ₃ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2,3-Cl ₂ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-2,4-Cl ₂ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ (Ph-3,4-Cl ₂ ) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ -(L-45a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ -(L-46a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ -(L-47a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) Ph HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) Ph HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ ) Ph HH 2-CH ₃ -4-OCHF ₂ (R) -CH (CH ₃ ) Ph HH 2-CH ₃ -4-OCHF ₂ (S) -CH (CH ₃ ) Ph HH 2-CH ₃ -4-OCHF ₂ CH (CH ₃ ) Ph H CH ₃ 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (Ph-2-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (Ph-3-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ ) (Ph-4-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ )-(L-1a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ )-(L-3a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ )-(L-45a) HH 2-CH ₃ -4-CF ₂ CF ₃ CH (CH ₃ )-(L-45a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH (CH ₃ )-(L-45a) HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ Ph HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ (Ph-3-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ C (CH ₃ ) ₂ (Ph-4-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ Ph HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ (Ph-2-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ (Ph-3-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ (Ph-4-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ -(L-46a) HH 2-CH ₃ -4-CF (CF ₃ ) ₂ CH ₂ CH ₂ -(L-46a) HH 2-CH ₃ -4-OCF ₃ C (CH ₃ ) ₂ CH ₂ Ph HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ CH ₂ Ph HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ OPh HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ O (Ph-2-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ O (Ph-3-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ O (Ph-4-Cl) HH 2-CH ₃ -4-CF ₂ CF ₃ CH ₂ CH ₂ NHPh HH 2-CH ₃ -4-CF ₂ CF ₃ L-3a HH 2-CH ₃ -4-CF ₂ CF ₃ M-4a HH 2-CH ₃ -4-CF ₂ CF ₃ M-8a HH 2-CH ₃ -4-CF (CF ₃ ) ₂ M-9a HH 2-CH ₃ -4-OCF ₃ M-9b HH 2-CH ₃ -4-CF (CF ₃ ) ₂ M-19a HH 2-CH ₃ -4-CF (CF ₃ ) ₂ OPr-n HH 2-CH ₃ -4-CF ₂ CF ₃ -CH ₂ CH ₂ CH ₂ CH ₂ -H 4-CF ₃ -CH ₂ CH ₂ CH ₂ CH ₂ -H 2-CH ₃ -4-CF ₂ CF ₃ -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -H 2-CH ₃ -4-CF ₂ CF ₃ -CH ₂ CH ₂ CH (CH ₃ ) CH ₂ CH ₂ -H 2-CH ₃ -4-CF ₂ CF ₃ -CH ₂ CH (CH ₃ ) CH ₂ CH (CH ₃ ) CH ₂ -H 2-CH ₃ -4-CF ₂ CF ₃ -CH ₂ CH ₂ OCH ₂ CH ₂ -H 2-CH ₃ -4-CF ₂ CF ₃ -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -H 2-CH ₃ -4-CF ₂ CF ₃ ―――――――――――――――――――――――――――――――――――

Table 2

[0150]

[Chemical 36]

[0151]

[Chemical 37]

[0152]

[Chemical 38]

[0153]

[Chemical Formula 39]

[0154]

[Table 2] ――――――――――――――――――――――――――――――――――― R ¹ R ² R ³ (Y) _n ― ―――――――――――――――――――――――――――――――――― Et Et H 6-Cl Et Et H 6-CF ₂ CF ₂ CF ₃ Et Et H 6-O (Ph-4-Br) Et Et H 2-Cl-6-CF ₂ CF ₂ CF ₃ Et Et H 2-Cl-6-CF (CF ₃ ) ₂ Et Et H 2-CH ₃ -6-OCH (CF ₃ ) ₂ i-Pr HHH i-Pr HH 4-SPr-i i-Pr HH 4-SBu-i i-Pr HH 6-Cl i-Pr HH 6-CF ₂ CF ₃ i -Pr HH 6-CF ₂ CF ₂ CF ₃ i-Pr HH 6-CF (CF ₃ ) ₂ i-Pr HH 6-OCHF ₂ i-Pr HH 6-OCH (CF ₃ ) ₂ i-Pr HH 6-O (Ph-4-Br) i-Pr HH 6-O (Ph-2,4-Cl ₂ ) i-Pr HH 6-SPr-i i-Pr HH 6-SBu-i i-Pr HH 6-SCHF ₂ i-Pr HH 6-SO ₂ CHF ₂ i-Pr HH 2-Cl-6-CF (CF ₃ ) ₂ i-Pr HH 2-Cl-6-OCF ₂ CHF ₂ i-Pr HH 2-Cl-6- OCH (CF ₃ ) ₂ i-Pr HH 2-Cl-6-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ i-Pr HH 2-CH ₃ -6-CF (CF ₃ ) ₂ i-Pr HH 2-CH _3- 6-OCHF ₂ i-Pr HH 2-CH ₃ -6-OCF ₂ CHF ₂ i-Pr HH 2-CH ₃ -6-OCH ₂ CF ₂ CF ₃ i-Pr HH 2-CH ₃ -6-OCF ₂ CHFCF ₃ i-Pr HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ i-Pr HH 2-CH ₃ -6-OCF ₂ CHFO CF ₂ CF ₂ CF ₃ i-Pr HH 2-CH ₃ -6-O (Ph-4-CF ₃ ) i-Pr HH 2-CH ₃ -6-SCHF ₂ i-Pr HH 2-OCH ₃ -6- CF (CF ₃ ) ₂ i-Pr HH 2-OCH (CF ₃ ) ₂ -6-CH ₃ i-Pr HH 2-SCH ₃ -6-CF (CF ₃ ) ₂ i-Pr HH 2-S (O) CH ₃ -6-CF (CF ₃ ) ₂ i-Pr HH 4-CH ₃ -6-Cl i-Pr HH 4-CH ₃ -6-CF (CF ₃ ) ₂ i-Pr HH 4-CH ₃ -6 -OCH (CF ₃ ) ₂ i-Pr HH 4-CH ₃ -6-O (Ph-4-Br) n-Bu HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ i-Bu HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ s-Bu HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ t-Bu HH 6-CF ₂ CF ₃ t-Bu HH 6-CF ₂ CF ₂ CF ₃ t -Bu HH 6-CF (CF ₃ ) ₂ t-Bu HH 2-Cl-6-CF (CF ₃ ) ₂ t-Bu HH 2-CH ₃ -6-CF (CF ₃ ) ₂ t-Bu HH 2- CH ₃ -6-OCH (CF ₃ ) ₂ t-Bu HH 4-CH ₃ -6-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Cl-6-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-Cl-6-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -6-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -6-OCH ₂ CF ₂ CF ₃ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 2-OCH ₃ -6-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SCH ₃ HH 4-CH ₃ -6-CF (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) CH ₃ HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ CH ₃ HH 2-CH _3- 6-OCH (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SEt HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ S (O) Et HH 2-CH ₃ -6- OCH (CF ₃ ) ₂ CH (CH ₃ ) CH ₂ SO ₂ Et HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 6-OCHF ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 6-SCHF ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-Cl-6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-Cl-6-OCF ₂ CHF ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-Cl-6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH _3- 6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-OCHF ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-OCF ₂ CHF ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-OCF ₂ CHFCF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-OCF ₂ CHFOCF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-O (Ph-4-CF ₃ ) C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-SCHF ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-CH ₃ -6-NHC (O) CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-OCH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-OCH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-OCH (CF ₃ ) ₂ -6-CH ₃ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2-SCH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 4-CH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 4-CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SCH ₃ HH 2,4-Cl ₂ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-Cl-6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -6-OCHF ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -6 -OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 2-CH ₃ -6-O (Ph-4-CF ₃ ) C (CH ₃ ) ₂ CH ₂ S ( O) CH ₃ HH 2-OCH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 4-CH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ S (O) CH ₃ HH 4-CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 6-OCHF ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-Cl-6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-Cl-6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -6-OCHF ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2 -CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -6-OCF ₂ CHFOCF ₂ CF ₂ CF ₃ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 2-CH ₃ -6-O (Ph-4-CF ₃ ) C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 4-CH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH ₂ SO ₂ CH ₃ HH 4-CH ₃ -6-OCH (CF ₃ ) ₂ CH (CH ₃ ) CH = NOH HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ CH (CH ₃ ) CH = NOCH ₃ HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOH HH 2-CH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOH HH 2 -CH ₃ -6-OCH (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -6-CF (CF ₃ ) ₂ C (CH ₃ ) ₂ CH = NOCH ₃ HH 2-CH ₃ -6-OCH (CF ₃ ) ₂ ―――――――――――――――――――――――――――――――――――

Table 3

[0156]

[Chemical 40]

[0157]

[Chemical 41]

[0158]

[Chemical 42]

[0159]

[Table 3] ――――――――――――――――――――――――――――― (Z) _p1 (Y) _n ――――――――― ―――――――――――――――――――― 2-CH ₂ OH 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₂ OCH ₃ 2-CH ₃ -4 -CF (CF ₃ ) ₂ 2-CHO 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH = NOCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-C (O) OCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₂ C (O) OCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₂ C (O) NHCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₂ C (O) N (CH ₃ ) ₂ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CN 2-CH ₃ -4-CF ₂ CF ₃ 2-CN 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CN 2-CH ₃ -4-OCF ₃ 3-Et 2-CH ₃ -4-CF ₂ CF ₃ 3-Et 2-CH _3- 4-CF (CF ₃ ) ₂ 3-Et 2-CH ₃ -4-OCF ₃ 3-Pr-n 2-CH ₃ -4-CF (CF ₃ ) ₂ 3-Pr-i 2-CH ₃ -4- CF (CF ₃ ) ₂ 3-Bu-n 2-CH ₃ -4-CF (CF ₃ ) ₂ 3-CH ₂ OH 2-CH ₃ -4-CF (CF ₃ ) ₂ 3-CH ₂ OCH ₃ 2- CH ₃ -4-CF (CF ₃ ) ₂ 3-CH (OH) CH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 3-CHO 2-CH ₃ -4-CF (CF ₃ ) ₂ 3- C (O) CH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 3-CH = NOCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 3-C (CH ₃ ) = NOCH ₃ 2- CH ₃ -4-CF (CF ₃ ) ₂ 3-Ph 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₃ -3-C (O) O Et 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₃ -3-CH ₂ C (O) OCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-C (O) OEt- 3-CN 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₃ -5-Et 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₂ CH ₂ CH ₂ CH ₂ -3 2 -CH ₃ -4-CF ₂ CF ₃ 2-CH ₂ CH ₂ CH ₂ CH ₂ -3 2-CH ₃ -4-CF (CF ₃ ) ₂ 2-CH ₂ CH ₂ CH ₂ CH ₂ -3 2-CH _{3 -4-OCF 3 2-CH} 2 CH 2 CH 2 CH (OH) -3 2-CH 3 -4-CF (CF 3) 2 2-CH 2 CH 2 CH 2 C (O) -3 2-CH _{3 -4-CF (CF 3)} 2 2-CH 2 CH 2 CH 2 C (= NOCH 3) -3 2-CH 3 -4-CF (CF 3) 2 2,3,4- (CH 3) 3 2-CH ₃ -4-CF (CF ₃ ) ₂ 2,4- (CH ₃ ) ₂ -3-C (O) OCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2,5- (CH ₃ ) ₂ -3-C (O) OCH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ 2,3- (CH ₃ ) ₂ -3-SO ₂ CH ₃ 2-CH ₃ -4-CF ( CF ₃ ) ₂ 2-CH ₂ CH (CH ₃ ) CH ₂ CH ₂ -3-4-CH ₃ 2-CH ₃ -4-CF (CF ₃ ) ₂ ――――――――――――――― ――――――――――――――――

The compounds of the present invention are so-called agricultural pests that harm agricultural and horticultural crops and trees, so-called livestock pests that parasitize livestock and poultry, and so-called sanitary pests that have various adverse effects on human living environments such as houses and warehouses. It is possible to effectively control so-called stored-grain pests that damage grains and the like stored in, and pests such as mites, nematodes, molluscs, and crustaceans that occur and harm in the same scene at low concentrations.

Insects which can be controlled by using the compound of the present invention,
Specific examples of mites, nematodes, molluscs and crustaceans include cotton bollworm, Bollworm, Tobacco moth, Cotton ball worm, Tobacco bud worm, Cotton leaf worm, Hasmonyoto, Fall army worm,
White armyworm, Southern army worm, Soy bean looper, Cabbage looper, Nicomoga, Covenomiga, Hymadalanomaga, Awayyoto, European corn borer, Tamanayaga, Kaburayaga, Mikanmokiga, Mimoko-noshikomako, Mimoko-nosimakoniga, Mimosa sinking moth, Codling moth. , Chahamaki, Grapeberry moss, Spodoptera litura, Pieris brassicae, Plutella xylostella, Tobacco hornworm, Phytophthora typhimurium, Ichimonjisetsueri, Tamanaginuwawa, American white weevil, Lepidoptera pests, Weevil Weevil, Weevil Weevil, Weevil Weevil, Weevil Weevil, Weevil Weevil, Weevil Weevil, Weevil Weevil, Weevil Weevil Weeville, Mexican bean beetle, weevil, a Weevil, Weevil Weevil, Southern Corn Rootworm, Western Corn Rootworm, Northern Corn Rootworm, Nijuyahoushitentou, Colorado Potato Beetle, Japanese Beetle, Urihamushi, Giant Beetle Beetle, Douga Nebububu, Himeboshi, Mamega, Tobacco Wolverine, Tobacco Beetle, Toadworm Pteridophyta such as rice beetle, stag beetle, stag beetle, beetle beetle, pine beetle, beetle, beetle, beetle, beetle, beetle, beetle, beetle, beetle, beetle , Beetle bug, leafhopper leafhopper, potato leafhopper, leafhopper leafhopper, chanomide Himeyokobai, small brown planthopper, Sejirounka, brown planthopper,
Tobacco whitefly, silver leaf whitefly, mandarin's whitefly, pear whitefly, mandarin's whitefly, azalea gumbai, onsite whitefly, cotton aphid, yellow peach aphid, moss aphid, beetle, moss, citrus aphid, moss, moss, moss Hemiptera pests such as sea turtles and bed bugs
Thrips pests such as Thrips palmi, Negra thistle, Miscanthus thrips, Thrips periwinkle, Thrips japonicum, etc. , Sheep horn fly, moss fly, bull fly, sheep fly,
Tsetse flies, yellow-tailed flycatcher, black-footed flies, giant fly, flies, mosquitoes, mosquitoes, Aedes albopictus, Aedes aegypti, Anopheles mosquitoes, etc. Pests of the order Pteroptera, black cockroaches, cockroaches, German cockroaches, etc. , Human flea, Keops nezuminomi and other isoptera pests, chicken white-footed lice, bovine lice and other halitosis pests, bovine lice, porcine lice, cattle beetle, kebuka Lice pests such as lice, citrus spider mites, apple spider mites, spider mites, mites such as kanzawa mites, citrus rust mite, fungus mites such as mite dust mite, tulip rust mite, tea mite dust mite, dust mite mite such as dust mite mite, moss dust mite mite Acarid mites, honeybee mites such as honeybee mites, ticks such as ox tick, phytophthora ixodidae, ticks mites such as oak medusa, mites such as mites, sweet potatoes nematodes, nematodes nematodes, nematodes nematoda , Nematodes such as potato cyst nematode, soybean cyst nematode, pine wood nematode, etc. Crustaceans molluscs, Armadillidium vulgare such as Sujimaimai, but and the like, the present invention is not limited thereto.

Furthermore, the compound of the present invention is also effective against harmful insects which have developed resistance to existing insecticides such as organic phosphorus compounds, carbamate compounds and pyrethroid compounds.

That is, the compound of the present invention comprises the orthoptera, thrips, hemiptera, lepidoptera, coleoptera, hymenoptera, diptera,
It is possible to effectively control pests of the order Thysanoptera, Isoptera, termites, mites, lice and nematodes at low concentrations. On the other hand, the compound of the present invention has extremely useful characteristics with almost no adverse effects on mammals, fish, crustaceans and beneficial insects.

When the compound of the present invention is used, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent,
Binders, anti-caking agents, disintegrating agents, defoaming agents, preservatives and anti-decomposition agents are added to give a solution (soluble concentrat).
e), emulsion (emulsifiable concentrate), wettable powder (wet
table powder), water soluble powder, water dispersible granule, water soluble granule, suspension conc.
entrate), emulsion (oil in water), suspoemulsion (suspoemulsion), microemulsion (microemulsion), dust (dustable powder), granule (gel) It can be put to practical use in a formulation. Further, from the viewpoint of labor saving and improvement of safety, the formulation of any of the above dosage forms can be provided by enclosing it in a water-soluble package such as a water-soluble capsule or a bag of a water-soluble film.

Examples of the solid carrier include natural mineral substances such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. And inorganic salts, synthetic silica and synthetic silicates.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and the like.
Examples include esters such as γ-butyrolactone, acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.

These solid and liquid carriers may be used alone or in combination of two or more kinds.

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene fatty acid ester. Nonionic surfactants such as oxyethylene sorbitan fatty acid ester, alkyl sulfates, alkylbenzene sulfonates,
Lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid,
Anionic surfactants such as polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates and polystyrenesulfonates, alkylamine salts and alkyl quaternary ammonium salts Examples include cationic surfactants and amphoteric surfactants such as amino acid type and betaine type surfactants.

The content of these surfactants is not particularly limited, but is preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the preparation of the present invention. Further, these surfactants may be used alone or in combination of two or more kinds.

The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally it is 0.00 per hectare (ha) as the active ingredient amount.
About 5 to 50 kg is suitable.

Next, formulation examples of preparations using the compound of the present invention are shown. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight.

[Wettable Powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Examples of other materials include anti-caking agents and decomposition inhibitors. .

[Emulsion] Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Examples of other materials include spreading agents and decomposition inhibitors.

[Suspending Agent] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Examples of other materials include antifreezing agents and thickeners.

[Granule wettable powder] Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts As other materials, for example, a binder, a decomposition inhibitor and the like can be mentioned.

[Liquid] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Examples of other include, for example, antifreezing agents, spreading agents and the like.

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

[Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Other examples include drift inhibitors and decomposition inhibitors.

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

In the following formulation examples, "part" means part by weight.

[Formulation Example 1] Wettable powder Compound No. 1-01 of the present invention 20 parts Pyrophyllite 74 parts Sorpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry) (Trade name) Carplex # 80D 2 parts (synthetic hydrous silicic acid: Shionogi Seiyaku Co., Ltd. trade name) The above are uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion Compound of the present invention No. 1-01 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Sorpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) The above is mixed uniformly to form an emulsion.

[Formulation Example 3] Suspension agent Invention Compound No. 1-01 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000C 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Xanthan gum 0.2 parts Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspension agent.

[Formulation Example 4] Granule wettable powder Compound of the present invention No. 1-01 75 parts Hitenol NE-15 5 parts (anionic surfactant: Dai-ichi Kogyo Seiyaku Co., Ltd. trade name) Vanilex N 10 parts (Anionic surfactant: Nippon Paper Industries Co., Ltd. product name) Carplex # 80D 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. product name) After uniformly mixing and grinding the above, a small amount of water was added. Stir and mix, granulate with an extrusion-type granulator, and dry to obtain a wettable granule.

[Formulation Example 5] Granules Compound of the present invention No. 1-01 5 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed by stirring to form an extrusion granulator. Granulate with and dry to obtain granules.

[Formulation Example 6] Powder Invention Compound No. 1-01 3 parts Carplex # 80D 0.5 copy (Synthetic hydrous silicic acid: trade name of Shionogi Pharmaceutical Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above is uniformly mixed and pulverized to obtain a powder.

In use, the above formulation was diluted with water for 1 to 10
Spray directly with or without dilution 000 times.

When the compound of the present invention is used as a pesticide, other herbicides of various species, various insecticides, acaricides, nematicides, fungicides, plant growth may be used at the time of formulation or spraying, if necessary. You may mix and apply with a regulator, a synergist, a fertilizer, a soil conditioner, etc.

[0189] In particular, when mixed with other pesticides or plant hormones, application can be expected to reduce cost by reducing the amount of application, to expand the insecticidal spectrum due to the synergistic action of the mixed agents, and to have a higher pest control effect. At this time, it is possible to combine a plurality of known pesticides at the same time. The types of pesticides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm Chemicals H
and book) compounds and the like described in the 1999 edition. Specific examples of the common names are as follows, but the general names are not limited thereto.

Bactericide: Acibenzolar-S-methyl (ac
ibenzolar-S-methyl), acylaminobenzamide (acyla
minobenzamide, ambam, ampropyfos, anilazine, azaconazole, azoxystrobin
robin), benalaxyl, benodanil (be
nodanil), benomyl, benazole (ben
thiazole), benzamacril, binapacryl, biphenyl, bitertanol, bethoxazin
e), bordeaux mixture, blasticidin-S, bromoconazole
onazole), bupirimate, buthiobate, calcium polysulfide (calciu)
m polysulfide), captafol, captan, copper oxychloride
oxychloride), carpropamid (carpropamid), carbendazine (carbendazim), carboxin (carboxi)
n), CGA-279202 (test name), quinomethionate (c
hinomethionat), black bench azone (chlobenthiazon)
e), chlorfenazol, chloroneb, chlorothaloni
l), chlozolinate, cufraneb (c
ufraneb), cymoxanil, cyproconazol, cyprodinil,
Cyprofuram, dazomet,
Debacarb and dichloroph
en), diclobutrazol (diclobutrazol), diclofuranide (diclhlofluanid), diclomedine (diclomed
ine), dichloran, diethofencarb, diclocymet,
Difenoconazole, diflumethorin, dimethirimo
l), dimethomorph, diiconazole, diniconazole, M-diniconazole-
M), dinocap, diphenylamine (diph
enylamine), dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenpho
s), epoxyconazole (epoxiconazole), etaconazole (etaconazole), etirimol (ethirimol), etridienol (etridiazole), famoxazone (fam)
oxadone), fenarimol, febuconazole, fenamidone,
Fendazosulam, fenf
uram), fenhexamid, fenpiclonil, fenpropidin
in), fenpropimorph, fentin, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fludioxonil, fluoroimide
de), fluquinconazole, flusilazole, flusulfamide (flusu)
lfamide), flutolanil, flutriafol, folpet, fosetyl-aluminium, fuberidazole, furalaxy
l), flamethopyr, guazati
ne), hexachlorobenzene,
Hexaconazole, hymexazol, imazalil, imibenconazole, iminocadine
tadine), ipconazole, iprobenphos, iprodione, iprodione, isoprothiolane, iprovalicarb, kasugamycin,
Kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb
focarb), metiram, metominostrobin, microbutanil (myclobutani)
l), MTF-753 (test name), nabam, nickel bis (dimethyldithiocarbamate) (nickel bis
(dimethyldithiocarbamate)), nitrothal-isopropyl, nuarimo
l), NNF-9425 (test name), octirinone (octhili)
none), off-race (ofurace), oxadixyl (oxa)
dixyl), oxycarboxin, oxpoconazole fumarate,
Pefurzoate, penconazole
onazole), pencecuron, phthalide, piperalin, polyoxins, potassium hydrogen carbonate (potassiumhydroge)
n carbonate), probenazole (probenazole), prochloraz (prochloraz), procymidon (procymidon)
e), propamocarbhydrochlorid
e), propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil
l), pyroquilon, quinomethionate
(quinomethionate), quinoxyfen,
Quintozene, RH7281 (test name), sodium hydrogen carbonate, sodium hypochlorite, sulfur (sulfu)
r), spiroxamine, tebuconazole, tecnazene, tetraconazole, thiabendazole
abendazole), thiadiazin / milneb, thifluzamide, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfuranid, tolylfluanid, triadimefon,
Triadimenol, toriadimenol, triazoxide, tricyclazole,
Tridemorph, triflumizole
lumizole), triforine, triticonazole, validamyci
n), vinclozolin, zinc sulfate (zinc
sulfate), zineb, ziram, and shiitake mycelium extract.

Bactericidal agent: Streptomycin (st
reptomycin), tecloftalam, oxyterracycline and oxolinic acid.

Nematicides: aldoxycarb
b), kazusaphos, fostiazate (fo)
sthiazate), fosthietan, oxamyl and fenamiphos.

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

Insecticide: abamectin, acephate, acetamipir
id), aldicarb (aldicarb), allethrin (alle)
thrin), azinphos-methyl, bendiocarb, benfurcarb
acarb), bensultap, bifenthrin, buprofezin, butocarboxin, carbaryl
yl), carbofuran (carbofuran), carbosulfan (carbosulfan), cartap (cartap), chlorfenapyr (chlorfenapyr), chlorpyrif (chlorpyrif)
os), chlorfenvinphos, chlorfluazuron, chlorfluazuron, clothianidin, chromafenozid
e), chlorpyrifos-methyl,
Cycloprothrin, cyfluthrin (c
yfluthrin), beta-cyfluthrin
n), cypermethrin, cyromazine (c
yromazine), cyhalothrin, lambda
Cyhalothrin (lambda-cyhalothrin), deltamethrin (deltamethrin), diafenthiuro (diafenthiuro)
n), diazinon, diacroden
oden), diflubenzuron, dimethylvinphos, diophenolane (dio)
fenolan), disulfoton, dimethoate, emamectin benzoate (emam)
ectin-benzoate), EPN, esfen valerate (esfen
valerate), ethiofencarb, ethiprole, etofenprox (eto)
fenprox), etrimfos, fenitrothion, fenobucar
b), phenoxycarb, fenpropathrin, fenvale
rate), fipronil, fluacrypyrim, flucithrinat
e), flufenoxuron, flufenprox, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion
ion), furathiocarb, halofenozide, hexaflumuron (hexaflumur)
on), hydramethylnon, imidacloprid, isofenphos
os), indoxacarb, indoxacarb, isoprocarb, isoxathion, lufenuron, malathion
n), metal dehydrate (metaldehyde), methamidophos (me
thamidophos), methidathion, methacrifos, metal carbs
b), Methomyl, Methoprene
e), methoxychlor, methoxyfenozide, monocrotophos (monoc
rotophos), muscarure (muscalure), nidinotefuran (nidinotefuran), nitenpyram (nitenpyra)
m), omethoate, oxydemeton-methyl, oxamyl,
Parathion, parathion-methyl (parat
hion-methyl), permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimipho-methyl.
phos-methyl), profenofos, protrifenbute, pymetrozine (pym)
etrozine), pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen
ofen), spinosad, sulfotep (sulf)
otep), tebufenozide (tebfenozide), teflubenzuron (teflubenzuron), tefluthrin (tefluthori)
n), terbufos, tetrachlorvinphos, thiacloprid
d), thiocyclam, thiodicarb (thi
odicarb), thiamethoxam, thiofanox, thiometon,
Tolfenpyrad, tralomethrin (t
ralomethrin), trichlorfon, triazuron, triflumuro
n) and vamidothion etc.

[0195]

[Examples] The present invention will be described in more detail by specifically describing the synthesis examples and test examples of the compounds of the present invention as examples below, but the present invention is not limited thereto. [Synthesis example]

Synthesis Example 1 N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-3- (pyrrol-1-yl) phthalic acid diamide (invention compound No. 1-01) and N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-6- (pyrrole-1-
Il) phthalic acid diamide (invention compound No. 1-0
6).

Step 1; Preparation of N- (4-heptafluoroisopropyl-2-methylphenyl) -3-nitrophthalic acid imide. 4-Nitrophthalic anhydride (4.94 g) and 4-heptafluoroisopropyl-2-methylaniline (7.05 g) were dissolved in acetic acid (50 ml), and the mixture was stirred with heating under reflux for 3.5 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the remaining solid was washed with an isopropyl ether-hexane mixed solvent to obtain 9.25 g of the desired product as white crystals. Melting point 151.0 to 153.0 ° C. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.25 (dd, J = 7.8,
0.6Hz, 1H), 8.21 (dd, J = 7.8, 0.6Hz, 1H), 8.02 (t,
J = 7.8Hz, 1H), 7.62 (s, 1H), 7.59 (d, J = 8.7Hz, 1H),
7.31 (d, J = 8.7Hz, 1H), 2.30 (s, 3H).

Step 2; Preparation of 3-amino-N- (4-heptafluoroisopropyl-2-methylphenyl) phthalimide. 2.57 g of iron powder was added to 2 ml of acetic acid and 47 ml of water, and N- (4-heptafluoroisopropyl-2 was added under stirring at 70 ° C.
-Methylphenyl) -3-nitrophthalimide 5.1
A solution of 8 g of 37 ml of acetic acid and 104 ml of ethyl acetate was added. After stirring at 70 ° C. for 3 hours, the mixture was allowed to cool to room temperature, 100 ml of water and 100 ml of ethyl acetate were added, and the insoluble matter was removed by filtration through Celite. Separate the organic layer from the filtrate,
Wash with saturated aqueous sodium hydrogen carbonate solution (50 ml x 5)
After that, the solid obtained by dehydrating and drying with saturated saline and anhydrous magnesium sulfate in this order and distilling off the solvent under reduced pressure is washed with a diisopropyl ether-normal hexane mixed solvent to obtain 3.81 g of the desired product. Was obtained as flesh-colored crystals. Melting point 123.0-125.0 ° C ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 7.59 (s, 1H), 7.56
(d, J = 8.4Hz, 1H), 7.50 (dd, J = 8.4, 7.2Hz, 1H), 7.
34 (d, J = 8.4Hz, 1H), 7.26 (dd, J = 7.2, 0.6Hz, 1H),
6.94 (dd, J = 8.4, 0.6Hz, 1H), 5.33 (bs, 2H), 2.30
(s, 3H).

Step 3; N- (4-heptafluoroisopropyl-2-methylphenyl) -3- (pyrrole-1-
Il) Manufacture of phthalimide. 3-amino-N- (4-heptafluoroisopropyl-
2-Methylphenyl) phthalimide 3.39 g of acetic acid 3
2,5-dimethoxytetrahydrofuran 1.
07 g was added, and the mixture was stirred with heating under reflux for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residual solid was washed with diisopropyl ether to obtain 2.03 g of the desired product as yellow crystals. Melting point 128.0-129.0 ° C. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 7.90 (dd, J = 7.5,
1.5Hz, 1H), 7.86 (t, J = 7.5, 1.5Hz, 1H), 7.75 (dd,
J = 7.5, 1.5Hz, 1H), 7.60 (s, 1H), 7.57 (d, J = 8.7Hz,
1H), 7.36 (d, J = 8.1Hz, 1H), 7.22 (t, J = 2.1Hz, 2
H), 6.39 (t, J = 2.1Hz, 2H), 2.30 (s, 3H).

Step 4; N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-3
- (pyrrol-1-yl) phthalic acid diamide and N ¹ -
(4-heptafluoro-isopropyl-2-methylphenyl) -N ² - isopropyl-6- (pyrrol-1-yl)
Manufacture of phthalic diamide. 10 ml of isopropylamine was added to 10 ml of a solution of 1.00 g of N- (4-heptafluoroisopropyl-2-methylphenyl) -3- (pyrrol-1-yl) phthalimide and 1,4-dioxane at 80 ° C. Stir for 4 hours.
After completion of the reaction, the mixture was allowed to cool to room temperature, the solvent was evaporated under reduced pressure, the residual solid was washed with chloroform, and N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-6- (pyrrole 0.50 g of -1-yl) phthalic acid diamide was obtained as white crystals. Melting point 217.0 to 220.0 ° C. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 7.88 (dd, J = 8.4,
6.0Hz, 1H), 7.4-7.55 (m, 4H), 7.41 (d, J = 9.0Hz, 1
H), 7.34 (bs, 1H), 6.94 (t, J = 2.1Hz, 2H), 6.36 (br,
2H), 6.32 (t, J = 2.1Hz, 2H), 4.2-4.25 (m, 1H), 2.0
1 (s, 3H), 1.22 (d, J = 6.6Hz, 6H). The above chloroform washing solution was collected, the solvent was distilled off under reduced pressure, and the residue was converted into ethyl acetate-normal hexane (1:
Purified by silica gel column chromatography eluting with 2), N ^1- (4-heptafluoroisopropyl-
2-methylphenyl) -N ² - isopropyl-3- (pyrrol-1-yl) phthalic acid diamide 0.32g as white crystals. Melting point 233.0-236.0 ° C. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.12 (bs, 1H), 8.2
5 (d, J = 7.8Hz, 1H), 7.88 (d, J = 7.8Hz, 1H), 7.57
(t, J = 7.8Hz, 1H), 7.45-7.55 (m, 2H), 7.44 (s, 1H),
6.91 (t, J = 2.1Hz, 2H), 6.32 (t, J = 2.1Hz, 2H), 5.59
(d, J = 8.1Hz, 1H), 3.9-4.05 (m, 1H), 2.43 (s, 3H),
0.90 (d, J = 6.6Hz, 6H).

[0202] Synthesis Example 2 3- (2-Chloro-pyrrol-1-yl) -N ¹ - (4-heptafluoroisopropyl-2-methylphenyl) -N ²
-Isopropylphthalic acid diamide (Compound No. 1 of the present invention)
-02) and 3- (2,5-dichloro-1-yl) -N ¹ - (4-heptafluoroisopropyl-2-methylphenyl) -N ² - isopropyl phthalic acid diamide (present compound No.1- 04). N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-3- (pyrrol-1-yl) phthalic acid diamide (invention compound No. 1-01)
To a solution of 39 g of tetrahydrofuran in 15 ml was added 0.13 g of N-chlorosuccinimide, and the mixture was stirred at room temperature for 15 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was mixed with water (1).
5 ml was added, and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order, and the solid obtained by distilling off the solvent under reduced pressure was eluted with ethyl acetate-normal hexane (1: 3) silica gel column chromatography. Purified by chromatography, 3
- (2-Chloro-pyrrol-1-yl) -N ¹ - (4-heptafluoroisopropyl-2-methylphenyl) -N ² -
White crystals 0.14g of isopropyl phthalic acid diamide, and 3- (2,5-dichloro-1-yl) -N ¹ -
White crystals (0.08 g) of (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropylphthalic acid diamide were obtained. 3- (2-Chloro-pyrrol-1-yl) -N ¹ - (4-heptafluoroisopropyl-2-methylphenyl) -N ²
-Isopropylphthalic acid diamide; melting point 216.0-218.0 ° C ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 9.05 (bs, 1H), 8.3
1 (dd, J = 8.4, 4.8Hz, 1H), 8.05 (d, J = 7.8Hz, 1H),
7.65 (t, J = 7.8Hz, 1H), 7.50-7.45 (m, 2H), 7.43 (s,
1H), 6.81 (dd, J = 3.0, 2.1Hz, 1H), 6.24 (dd, J = 3.
9, 3.3Hz, 1H), 6.15-6.25 (m, 1H), 5.62 (d, J = 7.2H
z, 1H), 3.90-4.00 (m, 1H), 2.42 (s, 3H), 0.80-1.00
. (bs, 6H) 3- ( 2,5- dichloro-1-yl) -N ¹ -
(4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropylphthalic acid diamide; melting point 217.0-219.0 ° C. ¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.99 (bs, 1H ), 8.2
9 (dd, J = 8.7, 4.4Hz, 1H), 8.11 (d, J = 8.1Hz, 1H),
7.69 (t, J = 8.1Hz, 1H), 7.40-7.50 (m, 3H), 6.19 (s,
2H), 5.77 (d, J = 7.8Hz, 1H), 3.95-4.05 (m, 1H), 2.
42 (s, 3H), 0.95 (d, J = 6.6Hz, 6H).

Synthesis Example 3 N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-3- (tetrazole-1
-Yl) phthalic acid diamide (invention compound No. 1-0
8) and N ^1- (4-heptafluoroisopropyl-2-
Methylphenyl) -N ² -isopropyl-6- (tetrazol-1-yl) phthalic acid diamide (the compound of the present invention No.
1-09).

Step 1; N- (4-heptafluoroisopropyl-2-methylphenyl) -3- (tetrazole-
1-yl) Production of phthalimide. 2.0 g of 3-amino-N- (4-heptafluoroisopropyl-2-methylphenyl) phthalimide prepared from 3-nitrophthalic anhydride in the same manner as in Steps 1 and 2 of Synthesis Example 1 and triethyl orthoformate. After stirring 3 ml at room temperature for 30 minutes, 4.3 ml of acetic acid and 0.47 g of sodium azide were added, and the mixture was further stirred at 80 ° C. for 2 hours. After completion of the reaction, the mixture was allowed to cool to room temperature, diluted with 20 ml of water and extracted with 20 ml of ethyl acetate. The organic layer was dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The residual solid was washed with diisopropyl ether to obtain 1.7 g of the desired product as white crystals. Melting point 178.0-179.0 ° C. ¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 9.87 (s, 1H), 8.46
(dd, J = 8.0, 1.0Hz, 1H), 8.18 (dd, J = 8.0, 1.0Hz, 1
H), 8.10 (t, J = 8.0Hz, 1H), 7.64 (s, 1H), 7.60 (d,
J = 8.3Hz, 1H), 7.37 (d, J = 8.2Hz, 1H), 2.30 (s, 1H).

Step 2; N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-3
-(Tetrazol-1-yl) phthalic acid diamide and N ¹
- (4-heptafluoroisopropyl-2-methylphenyl) -N ² - isopropyl-6- (tetrazol-1
Il) Production of phthalic diamide. To a solution of 0.7 g of N- (4-heptafluoroisopropyl-2-methylphenyl) -3- (tetrazol-1-yl) phthalimide in 20 ml of 1,4-dioxane was added 0.18 g of isopropylamine, and the mixture was allowed to reach room temperature. And stirred for 12 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residual solid was purified by silica gel column chromatography eluting with ethyl acetate to give N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl. 0.15 g of white crystals of 3- (tetrazol-1-yl) phthalic acid diamide, followed by N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-6-
0.30 g of white crystals of (tetrazol-1-yl) phthalic acid diamide were obtained. N ¹ - (4-heptafluoroisopropyl-2-methylphenyl) -N ² - isopropyl-3- (tetrazol -1
-Yl) phthalic acid diamide; melting point 241.0 to 242.0 ° C ¹ H NMR (DMSO-d ₆ , Me ₄ Si, 300 MHz) δ 10.10 (s, 1H),
9.60 (s, 1H), 8.21 (d, J = 7.5Hz, 1H), 7.95-8.0 (m, 1
H), 7.8-7.85 (m, 3H), 7.5-7.55 (m, 2H), 3.65-3.8
(m, 1H), 2.39 (s, 3H), 0.80 (d, J = 6.3Hz, 6H). N ^1- (4-heptafluoroisopropyl-2-methylphenyl) -N ² -isopropyl-6- (tetrazole -1
-Yl) phthalic acid diamide; melting point 216.0-217.0 ° C ¹ H NMR (DMSO-d ₆ , Me ₄ Si, 300 MHz) δ 9.94 (s, 1H), 9.
74 (s, 1H), 8.48 (d, J = 7.7Hz, 1H), 7.75-7.95 (m, 3
H), 7.4-7.55 (m, 3H), 3.95-4.1 (m, 1H), 2.06 (s, 3
H), 1.15 (d, J = 6.6Hz, 6H).

[0205] Synthesis Example 4 3- (2,5-dimethyl-3-trifluoroacetyl-1-yl) -N ¹ - (4-heptafluoroisopropyl-2-methylphenyl) -N ² - isopropyl phthalic acid diamide (Inventive compound No. 1-05).

Step 1; Preparation of 2- (2,5-dimethylpyrrol-1-yl) -N-isopropylbenzamide. To a solution of 2-amino-N-isopropylbenzamide (6.46 g) in toluene (70 ml) were added 2,5-hexanedione (5.0 g) and acetic acid (7 ml), and the mixture was stirred with heating under reflux for 15 hours.
After the reaction was completed, the mixture was allowed to cool to room temperature and diluted with 100 ml of ethyl acetate. The organic layer was water (100 ml), 1N hydrochloric acid (100 ml),
Water (50 ml), saturated aqueous sodium hydrogen carbonate solution (100
(ml), followed by dehydration and drying in order of saturated saline and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The remaining dark red oil was converted to ethyl acetate-normal hexane (1:
Purification by silica gel column chromatography eluting in 4) gave 5.56 g of the desired product as white crystals. Melting point 91.0-92.5 ° C ¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ8.24-8.30 (m, 1H),
7.51-7.59 (m, 2H), 7.19-7.24 (m, 1H), 6.00 (s, 2
H), 4.81 (bs, 1H), 3.97-4.10 (m, 1H), 1.94 (s, 6
H), 0.94 (d, J = 6.4Hz, 6H).

Step 2; Preparation of 3- (2,5-dimethylpyrrol-1-yl) -2-isopropylcarbamoylbenzoic acid. To a solution of 2- (2,5-dimethylpyrrol-1-yl) -N-isopropylbenzamide (2.56 g) in tetrahydrofuran (30 ml) was added dropwise 0.99 M secondary butyllithium hexane solution (20 ml) with stirring at -78 ° C.
After continuing stirring at −78 ° C. for 30 minutes, carbon dioxide gas was blown in at room temperature for 30 minutes. After continuing stirring at room temperature for another 30 minutes, 100 ml of water was added under ice cooling, and concentrated hydrochloric acid was added.
Adjust the pH to 2-3 and extract with ethyl acetate (100 ml x
3), the organic layer was dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The residual yellow solid is washed with diisopropyl ether to obtain the desired product 2.
58 g were obtained as cream crystals.

[0208] Step 3: 3- (2,5-dimethyl-3-trifluoroacetyl-1-yl) -N ¹ - (4-
Heptafluoroisopropyl-2-methylphenyl)-
Preparation of isopropyl phthalic diamides - N ^2. 3- (2,5-Dimethylpyrrol-1-yl) -2-isopropylcarbamoylbenzoic acid 4.52 g of toluene 1
To the 00 ml solution, 4.25 g of trifluoroacetic anhydride was added dropwise with stirring at room temperature. After stirring for 30 minutes at the same temperature, the solvent was distilled off under reduced pressure, the residue was dissolved in 110 ml of acetonitrile, and 4.13 g of 4-heptafluoroisopropyl-2-methylaniline and 10 drops of trifluoroacetic acid were added,
Stirring was continued overnight at room temperature. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residual solid was purified by silica gel column chromatography eluting with ethyl acetate-normal hexane (1: 6) to obtain 0.58 g of the desired product as white crystals. Melting point 238.5 to 239.5 ° C. ¹ H NMR (CDCl ₃ , Me ₄ Si, 400 MHz) δ 8.69 (bs, 1H), 8.2
2 (d, J = 8.4Hz, 1H), 8.03 (d, J = 8.0Hz, 1H), 7.71
(t, J = 8.0Hz, 1H), 7.46 (d, J = 8.8Hz, 1H), 7.44 (s, 1
H), 7.40 (dd, J = 8.0, 1.2Hz, 1H), 6.47 (q, J = 1.2Hz,
1H), 5.59 (d, J = 8.4Hz, 1H), 3.87-4.00 (m, 1H), 2.
38 and 2.39 (s, 6H), 2.05 and 2.06 (s, 3H), 0.85 an
d 0.88 (d, J = 6.6Hz, 6H).

The compound of the present invention can be produced according to the above-mentioned production method and Examples. Examples of such compounds are shown in Table 4, but the invention is not limited thereto.

In the table, i-Pr represents isopropyl, and X ¹
1 and X ¹ -4, respectively represent the following structures.

[0211]

[Chemical 43]

Table 4

[0213]

[Chemical 44]

[0214]

[Table 4] ――――――――――――――――――――――――――――――――――― No. X ¹ (Z) _p1 R ¹ ( Y) _n mp (℃) ――――――――――――――――――――――――――――――――――― 1-01 3- (X ¹ -1) H i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 233.0-236.0 1-02 3- (X ¹ -1) 2-Cl i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 216.0-218.0 1-03 3- (X ¹ -1) 2-Br i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 179.0-181.0 1-04 3- (X ¹ -1) 2,5-Cl ₂ i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 217.0-219.0 1-05 3- (X ¹ -1) 2,5- (CH ₃ ) ₂ -i-Pr 2 -CH ₃ -4-CF (CF ₃ ) ₂ 238.5-239.5 3-C (O) CF ₃ 1-06 6- (X ¹ -1) H i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 217.0-220.0 1-07 6- (X ¹ -1) 2,5- (CH ₃ ) ₂ i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 185.0-187.0 1-08 3- (X ¹ -4) H i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 241.0-242.0 1-09 6- (X ¹ -4) H i-Pr 2-CH ₃ -4-CF (CF ₃ ) ₂ 216.0-217.0 ―――――――――――――――――――――――――――――――――――

TEST EXAMPLE Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited thereto.

Test Example 1 Insecticidal test against Spodoptera litura A 10% emulsion of the compound of the present invention (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent to prepare a 500 ppm concentration drug solution. . About 1 kanlan leaf in this liquid
It was soaked for 0 seconds, air-dried, and then placed in a petri dish, in which 10 second-instar larvae of Spodoptera litura were released per petri dish, which was then placed in a thermostatic chamber at 25 ° C. with a lid having a hole. The number of dead insects was examined 6 days later, and the dead rate was calculated from the following formula. The test was conducted in a two-division system. Mortality rate (%) = (number of dead insects / number of released insects) × 100 As a result, the following compounds showed a mortality rate of 80% or more. Inventive Compound No .: 1-01, 1-06, 1-08

Test Example 2 Insecticidal test against diamondback moth A 10% emulsion of the compound of the present invention (25% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm. . About 1 kanlan leaf in this liquid
Soak for 0 seconds, air dry and place in a petri dish.
(Plutella xylostella) 2nd instar larva per petri dish
Zero larvae were released, and they were placed in a thermostatic chamber at 25 ° C with a perforated lid. The number of dead insects after 6 days was investigated, and the dead insect rate was calculated from the same formula as in Test Example 1. The test was conducted in a two-division system.
As a result, the following compounds showed a mortality of 80% or more. Inventive Compound No .: 1-01, 1-02, 1-03, 1
-06, 1-07, 1-08

[0218]

INDUSTRIAL APPLICABILITY In recent years, pests have acquired resistance due to the long-term use of insecticides and bactericides, making it difficult to control them with conventional insecticides and bactericides. In addition, some of the insecticides are highly toxic and remain in the environment for a long time, and the disturbance of the ecosystem due to these is a problem.
On the other hand, the compound of the present invention has excellent insecticidal and acaricidal activity against many agricultural pests and spider mites, and exerts a sufficient controlling effect against the pests that have acquired resistance to existing insecticides. To do. Furthermore, it has almost no adverse effect on mammals, fish and beneficial insects, has a low residue and has a low environmental load.

Therefore, the present invention can provide a useful novel pest control agent.

Front page continuation (51) Int.Cl. ⁷ Identification code FI theme code (reference) A01N 43/713 A01N 43/713 47/24 47/24 A 57/24 102 57/24 102Z 103 103A 104 104 A61K 31 / 402 A61K 31/402 31/41 31/41 A61P 33/14 A61P 33/14 C07D 207/333 C07D 207/333 207/34 207/34 257/04 257/04 A (72) Inventor Toshiro Miyake Minami Saitama Saitama Prefecture 1470 Shiraoka, Shiraoka, Gun-gun Nissan Chemical Industry Co., Ltd., Institute of Biological Sciences (72) Inventor Shinji Taki, Saitama Prefecture, Minami Saitama 1470 Shiraoka, Shirooka-cho, Nissan Chemical Industry Co., Ltd., Institute of Biological Sciences (72) Inventor, Toshinori Ito Minami Saitama 1470 Shiraoka, Shiraoka-cho, Saitama-gun Nissan Biochemical Laboratories F-term (reference) 4C069 AC05 AC06 AC07 AC08 BA01 BA08 BB02 BB08 BB15 BB16 BB22 BB28 BB45 BB49 BB56 BC01 BD03 BD09 4C086 AA01 AA02 AA03 BC05 GA13 BC08 BC17 BC08 MA01 MA04 MA17 MA22 MA23 MA28 MA37 MA41 MA43 M A63 NA07 NA14 ZB37 ZC61 4H011 AC01 BA01 BB09 BB13 BB17 BC01 BC07 BC09 BC17 BC18 BC19 BC20 DA02 DA15 DA16 DC01 DC04 DC05 DC06 DC08 DH03 DH14

Claims (4)

[Claims] 1. General formula (1): [Chemical 1] [In the formula, V¹, V², V³And V^FourAre each independently a carbon atom or
Represents a nitrogen atom, W¹And W²Are each independently an oxygen atom or a sulfur atom.
Then X¹Is the expression X¹-1 to expression X¹A heterocycle represented by any of -11
Represents [Chemical 2] X²Is a hydrogen atom, halogen atom, C₁~ C₆Alkyl, C₁~
C₆Haloalkyl, C₁~ C₆Alkoxy, C₁~ C₆Halo arco
Kisshi, C₁~ C₆Alkylthio or C₁~ C₆Haloalkylthio
, And when m is an integer of 2 or more, each X²Are each other
May be the same as or different from each other, Y is a hydrogen atom, a halogen atom, cyano, -SCN, -SF_Five,
Nitro, azide, C₁~ C ₆Alkyl, R^FiveArbitrarily placed by
Replaced (C₁~ C₆) Alkyl, C₃~ C₈Cycloalkyl, C₃
~ C₈Halocycloalkyl, C₂~ C₆Alkenyl, R^FiveBy
Arbitrarily replaced by (C₂~ C₆) Alkenyl, C₂~ C₆Archi
Nil, R^FiveArbitrarily replaced by (C₂~ C₆) Arkini
LE, -OH, -OR⁶, -OCHO, -SH, -SR⁶, -S (O) R⁶, -S (O)
₂R⁶, -NHR⁷, -N (R⁷) R⁶, -N (R⁷) CHO, -CHO, -C (O) R⁸, -C
(O) OR⁸, -C (O) SR⁸, -C (S) OR⁸, -C (S) SR⁸, -C (O) NHR⁹,-
C (O) N (R⁹) R⁸, -CH = NOR^Ten, -C (= NOR^Ten) R⁸, -C (= NOR^Ten) OR
⁸, -C (= NOR^Ten) SR⁸, -C (= NOR^Ten) NH (R⁹), -C (= NOR^Ten) N
(R⁹) R⁸, -P (O) (OR¹¹)₂, -P (S) (OR^{1 1})₂, -P (O) (R¹⁴) (OR
¹¹), -SiR¹²R¹³R¹⁴, (Z)_pMay be replaced by
Phenyl, (Z)_qNaphthi optionally substituted by
L, L or M, and n is an integer of 2 or more,
Y's may be the same or different
Well, and when n is 2 and two Ys are adjacent
, Two adjacent Y are -CH₂CH ₂CH₂-, -CH₂CH₂O-, -CH
₂OCH₂-, -OCH₂O-, -CH₂CH₂S-, -CH₂SCH₂-, -CH₂CH₂N
(R^Four)-, -CH₂N (R^Four) CH₂-, -CH₂CH = CH-, -OCH = CH-, -SCH = C
H-, -N (R^Four) CH = CH-, -OCH = N-, -SCH = N-, -N (R^Four) CH = N-, -N
(R^Four) N = CH-, -CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂O-, -CH₂OCH₂C
H₂-, -OCH₂CH₂O-, -CH₂OCH₂O-, -CH = CHCH = CH-, -N = CHCH
= CH- or -N = CHN = CH- forming a bond with Y
It may form a 5-membered ring or a 6-membered ring with the atom.
When the hydrogen atom bonded to each carbon atom is R¹⁵By
Optionally substituted, L is an aromatic compound represented by any of the formulas L-1 to L-58.
Represents a prime ring, [Chemical 3] [Chemical 4] M is an aliphatic compound represented by any of the formulas M-1 to M-28.
Represents a prime ring, [Chemical 5] R¹, R²And R³Are each independently a hydrogen atom, cyano, C₁~
C₁₂Alkyl, R¹⁶Arbitrarily replaced by (C₁~ C₁₂)
Alkyl, C₃~ C₈Cycloalkyl, C₃~ C₈Halo cycloa
Rukiru, C₃~ C₁₂Alkenyl, R¹⁶Arbitrarily replaced by
(C₃~ C₁₂) Alkenyl, C₃~ C₈Cycloalkenyl, C
₃~ C₈Halocycloalkenyl, C₃~ C₁₂Alkynyl, R¹⁶
Arbitrarily replaced by (C₃~ C₈) Alkynyl, -O
R¹⁷, -N (R¹⁸) R¹⁷, -SR¹⁹, -S (O)₂R¹⁹, -SN (R^{twenty one}) R²⁰, -S
N (R^{twenty three}) C (O) OR^{twenty two}, -S (O)₂N (R^{twenty five}) R^{twenty four}, -C (O) R⁸, -C (O) O
R⁸, -C (O) SR⁸, -C (S) R⁸, -C (S) OR⁸, -C (S) SR⁸, -C (O) N
(R^{twenty five}) R^{twenty four}Or R¹And R²Together with C₂
~ C₆Nitrogen bonded by forming an alkylene chain
It may form a 3- to 7-membered ring with the atom, and at this time,
The alkylene chain has 0 to 0 oxygen, sulfur or nitrogen atoms.
Two may be included, and depending on the halogen atom or methyl.
May be replaced by R^FourIs a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₆Alkenyl, C₃~ C₆Haloalkenyl, C₃~ C₆
Alkynyl, C₃~ C₆Haloalkynyl, C₁~ C₆Alkoxy
Carbonyl (C₁~ C_Four) Alkyl, C₁~ C₆Haloalkoxy
Lubonyl (C₁~ C_Four) Alkyl, C₁~ C₆Alkoxy, C₁~ C₆
Alkoxycarbonyl, C₁~ C₆Haloalkoxy carbon
Le, (Z)_pPhenyl optionally substituted by or
(Z)_pPositioned by phenyl, which may be substituted by
Replaced (C₁~ C_Four) Represents alkyl, R^FiveIs a halogen atom, C₃~ C₈Cycloalkyl, C₃~ C₈Ha
Cycloalkyl, -OH, -OR²⁶, -SH, -SR²⁶, -S (O)
R²⁶, -S (O)₂R²⁶, -NHR²⁷, -N (R²⁷) R²⁶, C₁~ C₆Arcoki
Sicarbonyl, C₁~ C₆Haloalkoxycarbonyl, -SiR
¹²R¹³R¹⁴, (Z)_pPheny optionally substituted by
Le, (Z)_qNaphthyl optionally substituted by L, L or
Represents M, R⁶Is C₁~ C₆Alkyl, R²⁸Arbitrarily replaced by
(C₁~ C₆) Alkyl, C₃~ C₈Cycloalkyl, C₃~ C₈Halo
Cycloalkyl, C₂~ C₆Alkenyl, R²⁸By any
Replaced by (C₂~ C₆) Alkenyl, C₃~ C₈Cycloarche
Nil, C₃~ C₈Halocycloalkenyl, C₃~ C₆Alkini
Le, R²⁸Arbitrarily replaced by (C₃~ C₆) Arkini
Le, -C (O) R⁸, -C (O) OR⁸, -C (O) N (R⁹) R⁸, -S (O)₂R⁸, -S
(O)₂N (R⁹) R⁸, -P (O) (OR¹¹)₂, -P (S) (OR¹¹)₂, (Z)_pBy
Optionally substituted phenyl, (Z) _qReplaced by
Optionally represents naphthyl, L or M, R⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₆Alkenyl, C₃~ C₆Haloalkenyl, C₃~ C₆
Alkynyl, C₃~ C₆Haloalkynyl, -CHO, C₁~ C₆Al
Kircarbonyl, C₁~ C₆Haloalkylcarbonyl, C₁~
C₆Alkoxycarbonyl, C₁~ C₆Haloalkoxy carbo
Nil, C₁~ C₆Alkylsulfonyl, C₁~ C₆Haloalkyl
Sulfonyl, (Z)_pPheny optionally substituted by
Lecarbonyl or (Z)_pMay be replaced by
Replaced by phenyl (C₁~ C_Four) Alkoxycarboni
Or R⁶And R⁷Together with C₂~ C_FiveA
With a nitrogen atom that binds by forming a rubylene chain
Together, they may form a 3- to 6-membered ring, in which case this alkyl group
The len chain may contain 0 to 2 oxygen atoms or sulfur atoms.
And substituted by halogen atom or methyl
Maybe, R⁸Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈Shi
Croalkyl, C₃~ C₈Halocycloalkyl, C₃~ C₈Shiku
Lower alkyl (C₁~ C_Four) Alkyl, C₁~ C₆Alkoxy (C₁~ C
_Four) Alkyl, C₁~ C₆Alkylthio (C₁~ C_Four) Alkyl, C₂
~ C₆Cyanoalkyl, C₂~ C₆Alkenyl, C₂~ C₆Haloa
Lucenil, C₂~ C₆Alkynyl, C₃~ C₆Haloalkynyl,
(Z)_pPhenyl optionally substituted by (Z)_pBy
Substituted by phenyl, which may be substituted by
(C₁~ C_Four) Alkyl, (Z)_qMay be replaced by
Represents naphthyl, L or M, R⁹Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₆Alkenyl or C₃~ C₆Represents alkynyl,
Or R⁸And R⁹Together with C₂~ C_FiveAlkylene chain
3 to 6-membered with the nitrogen atom to be bonded by forming
A ring may be formed, in which case the alkylene chain is oxygen.
It may contain 0 to 2 atoms or sulfur atoms, and
May be substituted by a hydrogen atom or methyl, R^TenIs a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₈Cycloalkyl, C₃~ C₆Alkenyl, C₃~ C₆
Haloalkenyl, C₃~ C₆Alkynyl, C₃~ C₆Halo Archi
Nil or (Z)_pTo phenyl which may be substituted by
Replaced by (C₁~ C_Four) Represents alkyl, R¹¹Is C₁~ C₆Alkyl or C₁~ C₆Table haloalkyl
Then R¹²And R₁₃Are each independently C₁~ C₆Represents alkyl, R¹⁴Is C₁~ C₆Alkyl or (Z)_pHas been replaced by
Represents phenyl, which may be R¹⁵Is a halogen atom, cyano, nitro, C₁~ C₆Archi
Le, C₁~ C₆Haloalkyl, C₂~ C₆Alkenyl, C₂~ C₆Ha
Lower alkenyl, C₂~ C₆Alkynyl, C₂~ C₆Halo alkini
Le, C₁~ C₆Alkoxy, C₁~ C₆Haloalkoxy, C₁~ C₆
Alkylthio, C₁~ C₆Haloalkylthio, C₁~ C₆Archi
Rusulfinyl, C₁~ C₆Haloalkylsulfinyl, C₁
~ C₆Alkylsulfonyl, C₁~ C₆Haloalkylsulfoni
Le, C₁~ C₆Alkylamino, di (C₁~ C₆) Alkylami
No, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Halo arcoki
Sicarbonyl, (Z)_pMay be replaced by
Nil, (Z)_qNaphthyl optionally substituted by L
Or M, and more than one R at the same time¹⁵Replaced by
Each R¹⁵Are identical to each other, or
They may be different, R¹⁶Is a halogen atom, cyano, nitro, C₃~ C₈Cyclo
Alkyl, C₃~ C₈Halocycloalkyl, -CHO, -C (O)
R⁸, -C (O) OR⁸, -C (O) SR⁸, -C (O) N (R⁹) R⁸, -C (O) C (O) O
R⁸, -CH = NOR^Ten, -C (= NOR^Ten) R⁸, -OR²⁹, -N (R³⁰) R²⁹, -S
H, -SR³¹, -S (O) R³¹, -S (O)₂R³¹, -P (O) (OR¹¹)₂, -P (S)
(OR¹¹)₂, -P (phenyl)₂, -P (O) (phenyl)₂, (Z)_pReplaced by
Optionally phenyl, (Z)_qHas been replaced by
May represent naphthyl, L or M, R¹⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₆Alkenyl, C₃~ C₆Haloalkenyl, C₃~ C₆
Alkynyl, (Z)_pPheny optionally substituted by
Or (Z)_pBy phenyl optionally substituted by
Was replaced by (C₁~ C_Four) Represents alkyl, R¹⁸Is C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo Archi
Lecarbonyl, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Ha
Lowalkoxycarbonyl or (Z)_pHas been replaced by
Represents optionally phenylcarbonyl, R¹⁹Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₆
Alkenyl, C₃~ C₆Haloalkenyl, C₃~ C₆Alkini
Le, (Z)_pPhenyl optionally substituted by (Z)_q
Represents naphthyl, L or M optionally substituted by
Then R²⁰And R^{twenty one}Are each independently C₁~ C₁₂Alkyl, C₁~ C₁₂
Haloalkyl, C₂~ C_{1 2}Cyanoalkyl, C₁~ C₁₂Arco
Kishi (C₁~ C₁₂) Alkyl, C₁~ C₁₂Alkoxy carbonyl
(C₁~ C₁₂) Alkyl, C₃~ C₁₂Alkenyl, C₃~ C₁₂Halo
Alkenyl, C₃~ C₁₂Alkynyl, C₃~ C₁₂Halo alkini
Le, C₁~ C₆Alkylcarbonyl, (Z)_pReplaced by
Optionally substituted by phenyl (C₁~ C_Four) Al
Kill or (Z)_pPhenyl which may be substituted by
Represents or R²⁰And R^{twenty one}Together with C_Four~ C₇Al
Covalently linking nitrogen atoms with the formation of a
A 5- to 8-membered ring may be formed in the
The chain may contain 0 to 2 oxygen or sulfur atoms,
And C₁~ C_FourOptionally substituted by alkyl, R^{twenty two}Is C₁~ C₁₂Represents alkyl, R^{twenty three}Is C₁~ C₆Alkyl or (Z)_pHas been replaced by
Optionally substituted by phenyl (C₁~ C_Four) Alkyl
Represents R^{twenty four}Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₂~ C₆Alkenyl, C₂~ C₆Alkynyl, C₃~ C₈Shiku
Lower alkyl, C₂~ C₆Cyanoalkyl, C₁~ C₆Alkoxy
(C₁~ C_Four) Alkyl, C₁~ C₆Alkylcarbonyl, C₁~ C₆
Alkoxy, C₁~ C₆Haloalkoxy, (Z)_pReplaced by
Optionally benzyloxy, (Z)_pReplaced by
Optionally phenyl or (Z)_pHas been replaced by
Represents benzyl, which may be R^{twenty five}Is a hydrogen atom, C₁~ C₆Alkyl or C₁~ C₆Halo al
Represents a kill or R^{twenty four}And R^{twenty five}Together with C_Four~
C₇A nitrogen source that binds by forming an alkylene chain
A 5- to 8-membered ring may be formed together with the child.
The rubylene chain may contain 0 to 2 oxygen or sulfur atoms.
Well and C₁~ C_FourMay be substituted by alkyl
The R²⁶Is C₁~ C₆Alkyl, R³²Arbitrarily replaced by
(C₁~ C₆) Alkyl, C₃~ C₈Cycloalkyl, C₃~ C₈Halo
Cycloalkyl, C₂~ C₆Alkenyl, R³²By any
Replaced by (C₂~ C₆) Alkenyl, C₃~ C₆Alkynyl,
R³²Arbitrarily replaced by (C₃~ C₆) Alkynyl, -C
(O) R⁸, -S (O)₂R⁸, (Z)_pMay be replaced by
Phenyl, (Z)_qNaphthi optionally substituted by
Represents L, L or M, R²⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₈Cycloalkyl, C₂~ C₆Alkenyl, C₃~ C₆
Alkynyl, (Z)_pPheny optionally substituted by
Le, (Z)_qNaphthyl optionally substituted by L, L or
Represents M or R²⁶And R²⁷Together with C₂~ C
_FiveA nitrogen source that binds by forming an alkylene chain
A 3- to 6-membered ring may be formed with the child at this time.
The rubylene chain may contain 0 to 2 oxygen or sulfur atoms.
Well and substituted by halogen atom or methyl
You can R²⁸Is a halogen atom, cyano, C₃~ C₈Cycloalk
Le, C₃~ C₈Halocycloalkyl, -OH, -OR³³, -SH, -SR
³³, -S (O) R³³, -S (O)₂R³³, -NHR³⁴, -N (R³⁴) R³³, -C (O)
R³³, -CHO, -C (O) OH, -C (O) OR³³Or (Z)_pReplaced by
Represents phenyl, which may be R²⁹Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₈Cycloalkyl, C₃~ C₈Halo cycloalk
Le, C₁~ C₆Alkoxy (C₁~ C₆) Alkyl, C₁~ C₆Archi
Lucio (C₁~ C₆) Alkyl, C₃~ C₆Alkenyl, C₃~ C₆Ha
Lower alkenyl, C₃~ C₆Alkynyl, C₃~ C₆Halo alkini
Le, -CHO, C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo al
Kircarbonyl, C₁~ C₆Alkoxycarbonyl, C₁~ C₆
Haloalkoxycarbonyl, C₁~ C₆Alkylaminocal
Bonil, Di (C₁~ C₆) Alkylaminocarbonyl, C₁~ C₆
Alkylaminothiocarbonyl, di (C₁~ C₆) Alkyla
Minothiocarbonyl, -P (O) (OR¹¹)₂, -P (S) (OR¹¹)₂,
(Z)_pPhenyl optionally substituted by (Z)_pBy
Substituted by phenyl, which may be substituted by
(C₁~ C_Four) Alkyl, (Z)_qMay be replaced by
Represents naphthyl, L or M, R³⁰Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₁~ C₆Alkylcarbonyl, C₁~ C₆Haloalkyl mosquito
Lebonil, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Haloa
Lucoxycarbonyl, C₁~ C₆Alkylsulfonyl, C₁~
C₆Haloalkylsulfonyl, (Z)_pHas been replaced by
May be phenylcarbonyl or (Z)_pReplaced by
Optionally substituted by phenyl (C₁~ C_Four) Al
Represents coxycarbonyl, or R²⁹And R³⁰Together with
Becomes C₂~ C_FiveBy forming an alkylene chain,
A 3- to 6-membered ring may be formed together with the nitrogen atom to be bonded,
In this case, the alkylene chain has 0 to 0 oxygen or sulfur atoms.
Two may be included, and depending on the halogen atom or methyl.
May be replaced by R³¹Is C₁~ C₈Alkyl, R³⁵Arbitrarily replaced by
(C₁~ C₈) Alkyl, C₃~ C₈Cycloalkyl, C₃~ C₈Halo
Cycloalkyl, C₃~ C₆Alkenyl, R³⁵By any
Replaced by (C₃~ C₆) Alkenyl, C₃~ C₆Alkynyl,
R³⁵Arbitrarily replaced by (C₃~ C₆) Alkynyl, -CH
O, -C (O) R³⁶, -C (S) R³⁶, -C (= NR³⁷) R³⁶, -SH, C₁~ C₆A
Luquilcio, C₁~ C₆Haloalkylthio, -P (O) (OR¹¹)₂,
-P (S) (OR¹¹)₂, (Z)_pMay be replaced by
Nil, (Z)_pPhenylthio optionally substituted by
Oh, (Z)_qNaphthyl optionally substituted by L, L or
Represents M, R³²Is a halogen atom, cyano, C₃~ C₈Cycloalk
Le, C₃~ C₈Halocycloalkyl, C₁~ C₆Alkoxy, C₁
~ C₆Haloalkoxy, C₁~ C₆Alkylthio, C₁~ C₆Halo
Alkylthio, C₁~ C₆Alkylsulfinyl, C₁~ C₆Ha
Roalkylsulfinyl, C₁~ C₆Alkylsulfonyl,
C₁~ C₆Haloalkylsulfonyl, C₁~ C₆Alkyl carbo
Nil, C₁~ C₆Haloalkylcarbonyl, C₁~ C₆Arcoki
Sicarbonyl, C₁~ C₆Haloalkoxycarbonyl, (Z)_p
Phenyl optionally substituted by (Z)_pBy
Optionally substituted phenoxy, (Z)_pReplaced by
Optionally phenylthio, (Z)_qReplaced by
Optionally represents naphthyl, L or M, R³³Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈
Cycloalkyl, C₃~ C ₈Halocycloalkyl, C₃~ C₆A
Lucenil, C₃~ C₆Haloalkenyl, C₃~ C₈Cycloarche
Nil, C₃~ C₈Halocycloalkenyl, C₃~ C₆Alkini
Le, C₃~ C₆Haloalkynyl, (Z)_pHas been replaced by
May be phenyl, (Z)_qMay be replaced by
Represents naphthyl, L or M, R³⁴Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₃~ C₈Cycloalkyl, C₃~ C₆Alkenyl, C₃~ C₆
Alkynyl, (Z)_pPheny optionally substituted by
Le, (Z)_qNaphthyl optionally substituted by L, L or
Represents M or R³³And R³⁴Together with C₂~ C
_FiveA nitrogen source that binds by forming an alkylene chain
A 3- to 6-membered ring may be formed with the child at this time.
The rubylene chain may contain 0 to 2 oxygen or sulfur atoms.
Well and substituted by halogen atom or methyl
You can R³⁵Is a halogen atom, cyano, nitro, C₃~ C₈Cyclo
Alkyl, C₃~ C₈Halocycloalkyl, -CHO, -C (O)
R⁸, -C (O) OR⁸, -C (O) SR⁸, -C (O) N (R⁹) R⁸, -C (O) C (O) O
R⁸, -CH = NOR^Ten, -C (= NOR^Ten) R⁸, -OR²⁹, -N (R³⁰) R²⁹, -S
H, -SR³⁸, -S (O) R³⁸, -S (O)₂R³⁸, -P (O) (OR¹¹)₂, -P (S)
(OR¹¹)₂, -P (phenyl)₂, -P (O) (phenyl)₂, (Z)_pReplaced by
Optionally phenyl, (Z)_qHas been replaced by
May represent naphthyl, L or M, R³⁶Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈
Cycloalkyl, C₃~ C ₈Halocycloalkyl, -OR³⁹,-
SR³⁹, -NHR⁴⁰, -N (R⁴⁰) R³⁹, (Z)_pHas been replaced by
May be phenyl, (Z)_qMay be replaced by
Represents naphthyl, L or M, R³⁷Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Arcoki
Si, C₁~ C₆Alkylamino, di (C₁~ C₆) Alkylami
No, C₁~ C₆Alkoxycarbonyl, C₁~ C₆Halo arcoki
Sicarbonyl or (Z)_pMay be replaced by
Represents phenyl, R³⁸Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈
Cycloalkyl, C₃~ C ₈Halocycloalkyl, C₃~ C₆A
Lucenil, C₃~ C₆Haloalkenyl, C₃~ C₆Alkynyl,
C₃~ C₆Haloalkynyl, C₁~ C₆Alkylcarbonyl, C₁
~ C₆Haloalkylcarbonyl, C₁~ C₆Alkoxy carbo
Nil, C₁~ C₆Haloalkoxycarbonyl, C₁~ C₆Archi
Luaminocarbonyl, di (C₁~ C₆) Alkylaminocarbo
Nil, (Z)_pPhenyl, optionally substituted by
(Z)_pPositioned by phenyl, which may be substituted by
Replaced (C₁~ C_Four) Represents alkyl, L or M, R³⁹Is C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₃~ C₈
Cycloalkyl, C₃~ C ₈Halocycloalkyl, C₃~ C₆A
Lucenil, C₃~ C₆Haloalkenyl, C₃~ C₆Alkynyl,
C₃~ C₆Haloalkynyl, (Z)_pEven if replaced by
Good phenyl, (Z)_pMay be replaced by
Substituted by nil (C₁~ C_Four) Represents alkyl, L or M
Then R⁴⁰Is a hydrogen atom, C₁~ C₆Alkyl, C₁~ C₆Halo Archi
Le, C₁~ C₆Alkylcarbonyl, C₁~ C₆Haloalkyl mosquito
Lebonil, C₁~ C₆Alkoxycarbonyl or C₁~ C₆Halo
Represents alkoxycarbonyl, or R³⁹And R⁴⁰And
C together₂~ C_FiveBy forming an alkylene chain
May form a 3- to 6-membered ring with the nitrogen atom to which it is attached.
At this time, this alkylene chain is an oxygen atom or a sulfur atom.
0 to 2 may be included, and a halogen atom or methyl
May be replaced by Z is a halogen atom, cyano, nitro, C₁~ C₆Archi
Le, C₁~ C₆Haloalkyl, C₁~ C₆Hydroxyalkyl,
C₁~ C_FourAlkoxy (C₁~ C_Four) Alkyl, C₁~ C_FourAlkoxy
Carbonyl (C₁~ C_Four) Alkyl, C₂~ C₆Alkenyl, C₂~
C₆Haloalkenyl, C₂~ C₆Alkynyl, C₂~ C₆Halo al
Quinyl, C₁~ C₆Alkoxy, C₁~ C₆Haloalkoxy, C₁
~ C₆Alkylthio, C₁~ C₆Haloalkylthio, C₁~ C₆A
Ruquilsulfinyl, C₁~ C₆Haloalkylsulfini
Le, C₁~ C₆Alkylsulfonyl, C₁~ C₆Haloalkyls
Lefonil, C₁~ C₆Alkylamino, di (C₁~ C₆) Alkyl
Amino, -CHO, C₁~ C₆Alkylcarbonyl, C₁~ C₆Halo
Alkylcarbonyl, -CH = NO (C ₁~ C₆Alkyl), -C (C₁
~ C₆Alkyl) = NO (C₁~ C₆Alkyl), C₁~ C₆Alkoxy
Carbonyl, C₁~ C₆Haloalkoxycarbonyl, C₁~ C₆
Alkylaminocarbonyl, di (C₁~ C₆) Alkylamino
Represents carbonyl or phenyl, p, p1, p2, p3, q, r1,
 When r2, r3 or r4 represent an integer of 2 or more, each Z is mutually exclusive.
May be the same or different, and
, If p1 is 2 and two Zs are adjacent, then
Two Zs in contact are -CH₂CH₂CH₂CH₂-, -CH₂CH₂CH₂C (O)-or
-CH₂CH₂CH₂C (= NO (C₁~ C₆To form an alkyl))-
May further form a 6-membered ring with the atom to which Z is bonded,
At this time, the hydrogen atom bonded to each carbon atom is a halogen atom.
Atom, C₁~ C_FourOptionally substituted by alkyl or hydroxyl
May be m represents an integer of 1 to 3, n represents an integer of 1 to 5, p represents an integer of 0 to 5, p1 represents an integer of 0 to 4, p2 represents an integer of 0 to 3, p3 represents an integer of 0 to 2, q represents an integer of 0 to 7, r represents an integer of 0 to 2, r1 represents an integer of 0 to 3, r2 represents an integer of 0 to 5, r3 represents an integer of 0 to 7, r4 represents an integer of 0 to 9. ] Phthalic acid dia represented by
Mid compounds or salts thereof. 2. A pest control agent comprising one or more of the phthalic acid diamide compound or its salt according to claim 1 as an active ingredient. 3. An agrochemical comprising one or more of the phthalic acid diamide compound or its salt according to claim 1 as an active ingredient. 4. An insecticidal or acaricidal agent, which comprises, as an active ingredient, one or more kinds of the phthalic acid diamide compound or the salt thereof according to claim 1.