U.S. patent application number 17/476407 was filed with the patent office on 2022-01-06 for diarylimidazole compound and harmful organism control agent.
This patent application is currently assigned to Nippon Soda Co., Ltd.. The applicant listed for this patent is Nippon Soda Co., Ltd.. Invention is credited to Hikaru Aoyama, Kazushige FUJII, Takao IWASA, Tomomi KOBAYASHI, Maki MATSUI, Keita SAKANISHI.
Application Number | 20220000112 17/476407 |
Document ID | / |
Family ID | |
Filed Date | 2022-01-06 |
United States Patent
Application |
20220000112 |
Kind Code |
A1 |
Aoyama; Hikaru ; et
al. |
January 6, 2022 |
DIARYLIMIDAZOLE COMPOUND AND HARMFUL ORGANISM CONTROL AGENT
Abstract
The present invention provides a compound represented by formula
(I) or salt thereof (in the formula, A.sup.1 and A.sup.2 each
independently represents a nitrogen atom or the like, B.sup.1,
B.sup.2, B.sup.3 and B.sup.4 each independently represents a carbon
atom or nitrogen atom, X.sup.1 represents an unsubstituted or
substituted C1-6 alkyl group or the like, n represents a number of
X.sup.1 and represents an integer of 0-4, R.sup.1 represents a
halogeno group or the like, R.sup.2 represents an unsubstituted or
substituted C1-6 alkyl group or the like, m represents a number of
the oxide group bonding with the nitrogen atom which does not bond
with R.sup.2 on the imidazole ring, and represents 0 or 1, R.sup.3
represents a hydrogen atom or the like, Ar represents an
unsubstituted or substituted C6-10 aryl group. ##STR00001##
Inventors: |
Aoyama; Hikaru; (Kanagawa,
JP) ; MATSUI; Maki; (Kanagawa, JP) ; IWASA;
Takao; (Kanagawa, JP) ; FUJII; Kazushige;
(Kanagawa, JP) ; KOBAYASHI; Tomomi; (Kanagawa,
JP) ; SAKANISHI; Keita; (Kanagawa, JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Nippon Soda Co., Ltd. |
Tokyo |
|
JP |
|
|
Assignee: |
Nippon Soda Co., Ltd.
Tokyo
JP
|
Appl. No.: |
17/476407 |
Filed: |
September 15, 2021 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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16797729 |
Feb 21, 2020 |
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17476407 |
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16004664 |
Jun 11, 2018 |
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16797729 |
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15501921 |
Feb 6, 2017 |
10021880 |
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PCT/JP2015/072762 |
Aug 11, 2015 |
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16004664 |
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International
Class: |
A01N 43/50 20060101
A01N043/50; A61K 31/4164 20060101 A61K031/4164; A61K 31/4439
20060101 A61K031/4439; C07D 233/64 20060101 C07D233/64; C07D 401/04
20060101 C07D401/04; A01N 43/54 20060101 A01N043/54; A01N 43/56
20060101 A01N043/56; A01N 43/58 20060101 A01N043/58; A01N 43/74
20060101 A01N043/74; C07D 401/14 20060101 C07D401/14; C07D 403/04
20060101 C07D403/04; C07D 405/04 20060101 C07D405/04; C07D 409/04
20060101 C07D409/04; C07D 417/14 20060101 C07D417/14 |
Foreign Application Data
Date |
Code |
Application Number |
Aug 13, 2014 |
JP |
2014-165034 |
Claims
1.-6. (canceled)
7. A compound represented by formula (II) or salt thereof.
##STR00024## in formula (II), B.sup.1 represents a nitrogen atom,
and B.sup.2, B.sup.3 and B.sup.4 each independently represents a
carbon atom, X.sup.1 represents an unsubstituted or substituted
C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group,
unsubstituted or substituted C2-6 alkynyl group, hydroxy group,
unsubstituted or substituted C1-6 alkoxy group, formyl group,
unsubstituted or substituted C1-6 alkyl carbonyl group,
unsubstituted or substituted C1-6 alkoxycarbonyl group,
unsubstituted or substituted C1-6 alkyl aminocarbonyl group,
mercapto group, unsubstituted or substituted C1-6 alkyl thio group,
unsubstituted or substituted C1-6 alkyl sulfinyl group,
unsubstituted or substituted C1-6 alkyl sulfonyl group,
unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted
or substituted C6-10 aryl group, unsubstituted or substituted 3-6
membered heterocyclyl group, unsubstituted or substituted amino
group, halogeno group, cyano group, or nitro group, n represents a
chemically acceptable number of X.sup.1 and represents an integer
of 0 to 4, when n is 2 or more, X.sup.1s may be the same or
different, and when n is 2 or more, two X.sup.1s may bond together
to form a ring, R.sup.1 represents a halogeno group, hydroxy group,
cyano group, substituted C1-6 alkyl group, unsubstituted or
substituted C1-6 alkoxy group, unsubstituted or substituted C1-6
alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl
group, unsubstituted or substituted C1-6 alkyl sulfonyl group,
unsubstituted or substituted C1-6 alkyl sulfonyloxy group, C1-6
alkyl aminocarbonyl group, C1-6 alkyl sulfoximino group or a group
represented by --S(.dbd.O)(.dbd.N--R.sup.a)--R.sup.b, in the
formula, R.sup.a represents a hydrogen atom, cyano group, C1-6
alkyl group or unsubstituted or substituted C1-6 alkyl carbonyl
group, R.sup.b represents a C1-6 alkyl group, R.sup.2 represents an
unsubstituted or substituted C1-6 alkyl group, unsubstituted or
substituted C2-6 alkenyl group, unsubstituted or substituted C2-6
alkynyl group, unsubstituted or substituted C3-8 cycloalkyl group,
hydroxy group, unsubstituted or substituted C1-6 alkoxy group,
formyl group, unsubstituted or substituted C1-6 alkyl carbonyl
group, unsubstituted or substituted C1-6 alkoxycarbonyl group, or
unsubstituted or substituted C1-6 alkyl sulfonyl group. R.sup.2 is
a substituent bonding with any one of the two nitrogen atoms on the
imidazole ring, m represents a number of the oxide group bonding
with the nitrogen atom which does not bond with R.sup.2 on the
imidazole ring, and represents 0 or 1, R.sup.3 represents a
hydrogen atom, unsubstituted or substituted C1-6 alkyl group,
unsubstituted or substituted C6-10 aryl group, halogeno group,
cyano group or nitro group, Ar represents an unsubstituted or
substituted C6-10 aryl group or unsubstituted or substituted 5-10
membered heteroaryl group, wherein substituents which form the
substituted groups mentioned above are selected from the group
consisting of: a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6
alkynyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a C6-10
aryl C1-6 alkyl group, a 3-6 membered heterocyclyl group, a 3-6
membered heterocyclyl C1-6 alkyl group, a hydroxy group, a C1-6
alkoxy group, a C2-6 alkenyloxy group, a C2-6 alkynyloxy group, a
C6-10 aryloxy group, a C6-aryl C1-6 alkoxy group, a 5-6 membered
heteroaryloxy group, a 5-6 membered heteroaryl C1-6 alkyloxy group,
a formyl group, a C1-6 alkyl carbonyl group, a formyloxy group, a
C1-6 alkyl carbonyloxy group, a C6-10 aryl carbonyl group, a C1-6
alkoxycarbonyl group, a C1-6 alkoxycarbonyloxy group, a carboxyl
group, a halogeno group, a C1-6 haloalkyl group, a C2-6 haloalkenyl
group, a C2-6 haloalkynyl group, a C1-6 haloalkoxy group, a C2-6
haloalkenyloxy group, a C1-6 haloalkyl carbonyl group, an amino
group, a C1-6 alkyl substituted amino group, a C6-10 aryl amino
group, a C6-10 aryl C1-6 alkyl amino group, a formyl amino group, a
C1-6 alkyl carbonyl amino group, a C1-6 alkoxycarbonyl amino group,
an unsubstituted or substituted aminocarbonyl group, an imino C1-6
alkyl group, an unsubstituted or substituted N-hydroxyimino C1-6
alkyl group, an aminocarbonyloxy group, a C1-6 alkyl substituted
aminocarbonyloxy group, a mercapto group, a C1-6 alkyl thio group,
a C1-6 haloalkyl thio group, a C6-10 aryl thio group, a 5-6
membered heteroaryl thio group, a C1-6 alkyl sulfinyl group, a C1-6
haloalkyl sulfinyl group, a C6-10 aryl sulfinyl group, a 5-6
membered heteroaryl sulfinyl group, a C1-6 alkyl sulfonyl group, a
C1-6 haloalkyl sulfonyl group, a C6-10 aryl sulfonyl group, a 5-6
membered heteroaryl sulfonyl group, an alkyl sulfonyloxy group, a
haloalkyl sulfonyloxy group, a tri C1-6 alkyl substituted silyl
group, a tri C6-10 aryl substituted silyl group, a cyano group, and
a nitro group.
8. A harmful organism control agent comprising as an active
ingredient at least one selected from the group consisting of the
compound and salt thereof defined in claim 7.
9. An insecticide or acaricide comprising as an active ingredient
at least one selected from the group consisting of the compound and
salt thereof defined in claim 7.
10. An external parasite control agent comprising as an active
ingredient at least one selected from the group consisting of the
compound and salt thereof defined in claim 7.
11. An internal parasite control agent or expellent comprising as
an active ingredient at least one selected from the group
consisting of the compound and salt thereof defined in claim 7.
Description
TECHNICAL FIELD
[0001] The present invention relates to a diarylimidazole compound
and a harmful organism control agent. More specifically, the
present invention relates to a diarylimidazole compound and a
harmful organism control agent containing the diarylimidazole
compound as an active ingredient. The diarylimidazole compound has
a superior acaricidal and/or insecticidal activity, superior
safety, and can be advantageously and industrially synthesized.
[0002] Priority is claimed on Japanese Patent Application No.
2014-165034, filed Aug. 13, 2014, the content of which is
incorporated herein by reference.
BACKGROUND ART
[0003] Various compounds having an acaricidal and/or insecticidal
activity have been suggested. In order to practically use these
compounds as an agrochemical, the compounds are required to have a
sufficient efficacy, and also to have other properties such as
being hard to cause drug-resistance, preventing phytotoxicity
against the plants and soil contamination, or having a low level of
toxicity against livestocks, fishes or the like.
[0004] Patent Document 1 discloses a compound represented by
formula (A). According to Patent Document 1, this compound has a
strong inhibitory activity to the generation of nitrogen monoxide
and has an effect for preventing and treating nitrogen monoxide
mediated disease.
##STR00002##
PRIOR ART LITERATURE
Patent Documents
[0005] Patent document 1: WO98/27108A
DISCLOSURE OF INVENTION
Problems to be Solved by the Invention
[0006] The objective of the present invention is to provide a
diarylimidazole compound or salt thereof as an active ingredient.
The diarylimidazole compound has a harmful organism control
activity, particularly, a superior acaricidal and/or insecticidal
activity, superior safety, and can be synthesized advantageously
and industrially. Furthermore, the objective of the present
invention is to provide a harmful organism control agent containing
the diarylimidazole compound or salt thereof.
Means for Solving the Problems
[0007] In order to achieve the above objective, the present
inventors conducted extensive studies. As a result, the present
inventors discovered that a diarylimidazole compound or salt
thereof having a specific structure demonstrates a superior
acaricidal and/or insecticidal activity, excellent properties and
high safety, and can be used as an active ingredient of harmful
organism control agent. Furthermore, the present inventors
discovered that the compound can be used as an active ingredient of
external parasite control agent. The present invention was achieved
on the basis of this perception.
[0008] That is, the present invention is as follows:
[1] A compound represented by formula (I) or salt thereof.
##STR00003##
[0009] in formula (I), A.sup.1 and A.sup.2 each independently
represents a nitrogen atom or CR.sup.3, provided that A.sup.1 and
A.sup.2 do not simultaneously represent a nitrogen atom or
simultaneously represent CR.sup.3,
[0010] B.sup.1, B.sup.2, B.sup.3 and B.sup.4 each independently
represents a carbon atom or a nitrogen atom, provided that when
B.sup.1 is a nitrogen atom, B.sup.2 and B.sup.4 represent a carbon
atom and B.sup.3 represents a carbon atom or a nitrogen atom, and
when B.sup.1 is a carbon atom, B.sup.2 to B.sup.4 represent a
carbon atom or a nitrogen atom except that two or more of B.sup.2
to B.sup.4 simultaneously represent a nitrogen atom,
[0011] X.sup.1 represents an unsubstituted or substituted C1-6
alkyl group, unsubstituted or substituted C2-6 alkenyl group,
unsubstituted or substituted C2-6 alkynyl group, hydroxy group,
unsubstituted or substituted C1-6 alkoxy group, formyl group,
unsubstituted or substituted C1-6 alkyl carbonyl group,
unsubstituted or substituted C1-6 alkoxycarbonyl group,
unsubstituted or substituted C1-6 alkyl aminocarbonyl group,
mercapto group, unsubstituted or substituted C1-6 alkyl thio group,
unsubstituted or substituted C1-6 alkyl sulfinyl group,
unsubstituted or substituted C1-6 alkyl sulfonyl group,
unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted
or substituted C6-10 aryl group, unsubstituted or substituted 3-6
membered heterocyclyl group, unsubstituted or substituted amino
group, halogeno group, cyano group, or nitro group,
[0012] n represents a chemically acceptable number of X.sup.1 and
represents an integer of 0 to 4, when n is 2 or more, X.sup.1s may
be the same or different, and when n is 2 or more, two X.sup.1s may
bond together to form a ring, R.sup.1 represents a halogeno group,
hydroxy group, cyano group, substituted C1-6 alkyl group,
unsubstituted or substituted C1-6 alkoxy group, unsubstituted or
substituted C1-6 alkyl thio group, unsubstituted or substituted
C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl
sulfonyl group, unsubstituted or substituted C1-6 alkyl sulfonyloxy
group, C1-6 alkyl aminocarbonyl group, C1-6 alkyl sulfoximino group
or a group represented by --S(.dbd.O)(.dbd.N--R.sup.a)--R.sup.b, in
the formula, R.sup.a represents a hydrogen atom, cyano group, C1-6
alkyl group or unsubstituted or substituted C1-6 alkyl carbonyl
group, R.sup.b represents a C1-6 alkyl group,
[0013] R.sup.2 represents an unsubstituted or substituted C1-6
alkyl group, unsubstituted or substituted C2-6 alkenyl group,
unsubstituted or substituted C2-6 alkynyl group, unsubstituted or
substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or
substituted C1-6 alkoxy group, formyl group, unsubstituted or
substituted C1-6 alkyl carbonyl group, unsubstituted or substituted
C1-6 alkoxycarbonyl group, or unsubstituted or substituted C1-6
alkyl sulfonyl group. R.sup.2 is a substituent bonding with any one
of the two nitrogen atoms on the imidazole ring,
[0014] m represents a number of the oxide group bonding with the
nitrogen atom which does not bond with R.sup.2 on the imidazole
ring, and represents 0 or 1,
[0015] R.sup.3 represents a hydrogen atom, unsubstituted or
substituted C1-6 alkyl group, unsubstituted or substituted C6-10
aryl group, halogeno group, cyano group or nitro group,
[0016] Ar represents an unsubstituted or substituted C6-10 aryl
group or unsubstituted or substituted 5-10 membered heteroaryl
group.
[2] The compound or salt thereof according to [1], wherein formula
(I) is formula (II) or formula (II),
##STR00004##
[0017] in formula (II) and formula (III), X.sup.1, R.sup.1,
R.sup.2, R.sup.3, B.sup.1, B.sup.2, B.sup.3, B.sup.4, n, m and Ar
are as defined in formula (I).
[3] A harmful organism control agent comprising as an active
ingredient at least one selected from the group consisting of the
compound and salt thereof defined in [1] or [2]. [4] An insecticide
or acaricide comprising as an active ingredient at least one
selected from the group consisting of the compound and salt thereof
defined in [1] or [2]. [5] An external parasite control agent
comprising as an active ingredient at least one selected from the
group consisting of the compound and salt thereof defined in [1] or
[2]. [6] An internal parasite control agent or expellent comprising
as an active ingredient at least one selected from the group
consisting of the compound and salt thereof defined in [1] or
[2].
Effects of the Invention
[0018] The diarylimidazole compound or salt thereof according to
the present invention can prevent harmful organisms which are
harmful for agricultural crops and cause the problem of hygiene.
Particularly, the compound or salt thereof according to the present
invention can effectively prevent acari and insecticides.
Furthermore, the compound or salt thereof according to the present
invention can prevent external parasites and internal parasite
which are harmful for humans and animals.
BEST MODE FOR CARRYING OUT THE INVENTION
[Formula (I)]
[0019] The diarylimidazole compound of the present invention is a
compound represented by formula (I) (thereinafter, may be referred
to as compound (I)) or salt of compound (I).
##STR00005##
[0020] Firstly, in the present invention, the term "unsubstituted"
indicates a group including only a mother nucleus. When a group is
referred to as a name of a mother nucleus without "substituted",
this refers to "unsubstituted" unless specifically indicated
otherwise.
[0021] On the other hand, the term "substituted" indicates that at
least one of the hydrogen atoms of the mother nucleus is
substituted with a substituent having a structure that is the same
as the structure of the mother nucleus or different from the
structure of the mother nucleus. Thus, a "substituent" is another
group bonded with the mother nucleus. There may be one substituent
or two or more substituents. Two or more substituents may be the
same as or different from each other.
[0022] For example, the term "C1-6" or the like indicates that the
number of carbon atoms of the mother nucleus is 1 to 6. The number
of carbon atoms present in substituents is not included in this
number of carbon atoms. For example, a butyl group having an ethoxy
group as a substituent thereof is classified as a C2 alkoxy C4
alkyl group.
[0023] The "substituent" is not particularly limited as long as it
is chemically acceptable and achieves the effects of the present
invention.
[0024] Examples of the "substituent" are as follows:
[0025] a C1-6 alkyl group such as a methyl group, ethyl group,
n-propyl group, i-propyl group, n-butyl group, s-butyl group,
i-butyl group, t-butyl group, n-pentyl group, n-hexyl group or the
like;
[0026] a C2-6 alkenyl group such as a vinyl group, 1-propenyl
group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl
group, 3-butenyl group, 1-methyl-2-propenyl group,
2-methyl-2-propenyl group or the like;
[0027] a C2-6 alkynyl group such as an ethynyl group, 1-propynyl
group, 2-propynyl group, 1-butynyl group, 2-butynyl group,
3-butynyl group, 1-methyl-2-propynyl group or the like;
[0028] a C3-8 cycloalkyl group such as a cyclopropyl group,
cyclobutyl group, cyclopentyl group, cyclohexyl group, cubanyl
group or the like;
[0029] a C6-10 aryl group such as a phenyl group, naphthyl group or
the like;
[0030] a C6-10 aryl C1-6 alkyl group such as a benzyl group,
phenethyl group or the like;
[0031] a 3-6 membered heterocyclyl group;
[0032] a 3-6 membered heterocyclyl C1-6 alkyl group;
[0033] a hydroxy group;
[0034] a C1-6 alkoxy group such as methoxy group, ethoxy group,
n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group,
i-butoxy group, t-butoxy group or the like;
[0035] a C2-6 alkenyloxy group such as vinyloxy group, allyloxy
group, propenyloxy group, butenyloxy group or the like;
[0036] a C2-6 alkynyloxy group such as ethynyloxy group,
propargyloxy group or the like;
[0037] a C6-10 aryloxy group such as phenoxy group, naphthoxy group
or the like; a C6-10 aryl C1-6 alkoxy group such as benzyloxy
group, phenethyloxy group or the like;
[0038] a 5-6 membered heteroaryloxy group such as thiazolyloxy
group, pyridyloxy group or the like;
[0039] a 5-6 membered heteroaryl C1-6 alkyloxy group such as
thiazolyl methyloxy group, pyridyl methyloxy group or the like;
[0040] a formyl group;
[0041] a C1-6 alkyl carbonyl group such as acetyl group, propionyl
group or the like;
[0042] a formyloxy group;
[0043] a C1-6 alkyl carbonyloxy group such as acetyloxy group,
propionyloxy group or the like;
[0044] a C6-10 aryl carbonyl group such as benzoyl group or the
like;
[0045] a C1-6 alkoxycarbonyl group such as methoxycarbonyl group,
ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl
group, n-butoxycarbonyl group, t-butoxycarbonyl group or the
like;
[0046] a C1-6 alkoxycarbonyloxy group such as methoxycarbonyloxy
group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group,
i-propoxycarbonyloxy group, n-butoxycarbonyloxy group,
t-butoxycarbonyloxy group or the like;
[0047] a carboxyl group;
[0048] a halogeno group such as fluoro group, chloro group, bromo
group, iodo group or the like;
[0049] a C1-6 haloalkyl group such as chloromethyl group,
chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl
group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group or the
like;
[0050] a C2-6 haloalkenyl group such as 2-chloro-1-propenyl group,
2-fluoro-1-butenyl group or the like;
[0051] a C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl
group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group or the
like;
[0052] a C1-6 haloalkoxy group such as trifluoromethoxy group,
2-chloro-n-propoxy group, 2,3-dichlorobutoxy group or the like;
[0053] a C2-6 haloalkenyloxy group such as 2-chloropropenyloxy
group, 3-bromobutenyloxy group or the like;
[0054] a C1-6 haloalkyl carbonyl group such as chloroacetyl group,
trifluoroacetyl group, trichloroacetyl group or the like;
[0055] an amino group;
[0056] a C1-6 alkyl substituted amino group such as methyl amino
group, dimethyl amino group, diethyl amino group or the like;
[0057] a C6-10 aryl amino group such as anilino group, naphthyl
amino group or the like;
[0058] a C6-10 aryl C1-6 alkyl amino group such as benzyl amino
group, phenethyl amino group or the like;
[0059] a formyl amino group;
[0060] a C1-6 alkyl carbonyl amino group such as acetyl amino
group, propanoyl amino group, butyryl amino group, i-propyl
carbonyl amino group or the like;
[0061] a C1-6 alkoxycarbonyl amino group such as methoxycarbonyl
amino group, ethoxycarbonyl amino group, n-propoxycarbonyl amino
group, i-propoxycarbonyl amino group or the like;
[0062] an unsubstituted or substituted aminocarbonyl group such as
aminocarbonyl group, dimethyl aminocarbonyl group, phenyl
aminocarbonyl group, N-phenyl-N-methyl aminocarbonyl group,
N-butyl-N-methyl aminocarbonyl group or the like; an imino C1-6
alkyl group such as iminomethyl group, (1-imino)ethyl group,
(1-imino)-n-propyl group or the like;
[0063] an unsubstituted or substituted N-hydroxyimino C1-6 alkyl
group such as N-hydroxy-iminomethyl group,
(1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl
group, N-methoxy-iminomethyl group, (1-(N-methoxy)-imino)ethyl
group or the like;
[0064] an aminocarbonyloxy group;
[0065] a C1-6 alkyl substituted aminocarbonyloxy group such as
ethyl aminocarbonyloxy group, dimethyl aminocarbonyloxy group or
the like;
[0066] a mercapto group;
[0067] a C1-6 alkyl thio group such as methyl thio group, ethyl
thio group, n-propyl thio group, i-propyl thio group, n-butyl thio
group, i-butyl thio group, s-butyl thio group, t-butyl thio group
or the like;
[0068] a C1-6 haloalkyl thio group such as trifluoromethyl thio
group, 2,2,2-trifluoroethyl thio group or the like;
[0069] a C6-10 aryl thio group such as phenyl thio group, naphthyl
thio group or the like;
[0070] a 5-6 membered heteroaryl thio group such as thiazolyl thio
group, pyridyl thio group or the like;
[0071] a C1-6 alkyl sulfinyl group such as methyl sulfinyl group,
ethyl sulfinyl group, t-butyl sulfinyl group or the like;
[0072] a C1-6 haloalkyl sulfinyl group such as trifluoromethyl
sulfinyl group, 2,2,2-trifluoroethyl sulfinyl group or the
like;
[0073] a C6-10 aryl sulfinyl group such as phenyl sulfinyl group or
the like; a 5-6 membered heteroaryl sulfinyl group such as
thiazolyl sulfinyl group, pyridyl sulfinyl group or the like;
[0074] a C1-6 alkyl sulfonyl group such as methyl sulfonyl group,
ethyl sulfonyl group, t-butyl sulfonyl group or the like;
[0075] a C1-6 haloalkyl sulfonyl group such as trifluoromethyl
sulfonyl group, 2,2,2-trifluoroethyl sulfonyl group or the
like;
[0076] a C6-10 aryl sulfonyl group such as phenyl sulfonyl group or
the like; a 5-6 membered heteroaryl sulfonyl group such as
thiazolyl sulfonyl group, pyridyl sulfonyl group or the like;
[0077] an alkyl sulfonyloxy group such as methyl sulfonyloxy group,
ethyl sulfonyloxy group, t-butyl sulfonyloxy group or the like;
[0078] a haloalkyl sulfonyloxy group such as trifluoromethyl
sulfonyloxy group, 2,2,2-trifluoroethyl sulfonyloxy group or the
like;
[0079] a tri C1-6 alkyl substituted silyl group such as trimethyl
silyl group, triethyl silyl group, t-butyl dimethyl silyl group or
the like;
[0080] a tri C6-10 aryl substituted silyl group such as triphenyl
silyl group or the like;
[0081] a cyano group; a nitro group.
[0082] In addition, any of the hydrogen atoms in these
"substituents" may be substituted with other substituents having a
different structure. In this case, examples of the "substituents"
include a C1-6 alkyl group, C1-6 haloalkyl group, C1-6 alkoxy
group, C1-6 haloalkoxy group, halogeno group, cyano group, nitro
group and the like.
[0083] In addition, the above described "3-6 membered heterocyclyl
group" is a group having 1-4 hetetro atoms selected from the group
consisting of a nitrogen atom, oxygen atom and sulfur atom as a
constitution atom of the ring. The heterocyclyl group may be a
monoheterocyclyl group or a polyheterocyclyl group. As long as the
polyheterocyclyl group includes at least one hetero ring, the
remaining ring may be a saturated alicyclic ring, an unsaturated
alicyclic ring or an aromatic ring. Examples of the "3-6 membered
heterocyclyl group" include a 3-6 membered saturated heterocyclyl
group, 5-6 membered heteroaryl group, 5-6 membered
partially-unsaturated heterocyclyl group and the like.
[0084] Examples of the "3-6 membered saturated heterocyclyl group"
include an aziridinyl group, epoxy group, pyrrolidinyl group,
tetrahydrofuranyl group, thiazolidinyl group, piperidyl group,
piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl
group and the like.
[0085] Examples of the "5 membered heteroaryl group" include a
pyrrolyl group, furyl group, thienyl group, imidazolyl group,
pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group,
isothiazolyl group, triazolyl group, oxadiazolyl group,
thiadiazolyl group, tetrazolyl group and the like.
[0086] Examples of the "6 membered heteroaryl group" include a
pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl
group, triazinyl group and the like.
[A.sup.1, A.sup.2]
[0087] A.sup.1 and A.sup.2 each independently represents a nitrogen
atom or CR.sup.3, provided that A.sup.1 and A.sup.2 do not
simultaneously represent a nitrogen atom or simultaneously
represent CR.sup.3.
[0088] That is, the compound represented by formula (I) may be the
compounds represented by the following formulas (II) to (V).
##STR00006##
[0089] In formulas (II) to (III), B.sup.1, B.sup.2, B.sup.3,
B.sup.4, X.sup.1, R.sup.1, R.sup.2, R.sup.3, n, m and Ar are as
defined in formula (I).
[B.sup.1, B.sup.2, B.sup.3, B.sup.4]
[0090] B.sup.1, B.sup.2, B.sup.3 and B.sup.4 each independently
represents a carbon atom or a nitrogen atom, provided that when
B.sup.1 is a nitrogen atom, B.sup.2 and B.sup.4 represent a carbon
atom and B.sup.3 represents a carbon atom or a nitrogen atom, and
when B.sup.1 is a carbon atom, B.sup.2 to B.sup.4 represent a
carbon atom or a nitrogen atom except that two or more of B.sup.2
to B.sup.4 simultaneously represent a nitrogen atom.
[0091] That is, the compound represented by formula (I) may be the
compounds represented by the following formulas (a) to (f).
##STR00007##
[0092] In formulas (a) to (f), A.sup.1, A.sup.2, X.sup.1, R.sup.1,
R.sup.2, R.sup.3, n, m and Ar are as defined in formula (I).
[0093] Among these compounds, the compound represented by formula
(I), wherein B.sup.1 represents a nitrogen atom or a carbon atom,
B.sup.2, B.sup.3 and B.sup.4 represent a carbon atom,
namely the compounds represented by formulas (a) and (b) are
preferable.
[0094] [X.sup.1, n]
[0095] X.sup.1 represents an unsubstituted or substituted C1-6
alkyl group, unsubstituted or substituted C2-6 alkenyl group,
unsubstituted or substituted C2-6 alkynyl group, hydroxy group,
unsubstituted or substituted C1-6 alkoxy group, formyl group,
unsubstituted or substituted C1-6 alkyl carbonyl group,
unsubstituted or substituted C1-6 alkoxycarbonyl group,
unsubstituted or substituted C1-6 alkyl aminocarbonyl group,
mercapto group, unsubstituted or substituted C1-6 alkyl thio group,
unsubstituted or substituted C1-6 alkyl sulfinyl group,
unsubstituted or substituted C1-6 alkyl sulfonyl group,
unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted
or substituted C6-10 aryl group, unsubstituted or substituted 3-6
membered heterocyclyl group, unsubstituted or substituted amino
group, halogeno group, cyano group or nitro group.
[0096] The "C1-6 alkyl group" of X.sup.1 may be a linear alkyl
group or a branched alkyl group when the carbon number is three or
more. Examples of the "alkyl group" include a methyl group, ethyl
group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl
group, i-propyl group, i-butyl group, s-butyl group, t-butyl group,
i-pentyl group, neopentyl group, 2-methyl butyl group, 2,2-dimethyl
propyl group, i-hexyl group and the like.
[0097] Specific examples of the "substituted C1-6 alkyl group"
include a C1-6 haloalkyl group such as fluoromethyl group,
chloromethyl group, bromomethyl group, difluoromethyl group,
dichloromethyl group, dibromomethyl group, trifluoromethyl group,
trichloromethyl group, tribromomethyl group, 1-chloroethyl group,
2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group,
pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group,
3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethyl
ethyl group, 1,1,1,3,3,3-hexafluoropropane-2-yl group,
perfluoropropane-2-yl group, perfluorohexyl group, perchlorohexyl
group, 2,4,6-trichlorohexyl group or the like;
[0098] a hydroxy C1-6 alkyl group such as hydroxymethyl group,
hydroxyethyl group or the like;
[0099] a C1-6 alkoxy C1-6 alkyl group such as methoxymethyl group,
ethoxymethyl group, methoxyethyl group, ethoxyethyl group,
methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl
group, s-butoxymethyl group, t-butoxyethyl group or the like;
[0100] a C6-10 aryl C1-6 alkyl group such as benzyl group,
phenethyl group or the like;
[0101] a C3-8 cycloalkyl C1-6 alkyl group such as cyclopropyl
methyl group, 2-cyclopropyl ethyl group, cyclopentyl methyl group,
2-cyclohexyl ethyl group, 2-cyclooctyl ethyl group or the like; and
the like.
[0102] Examples of the "C2-6 alkenyl group" of X.sup.1 include a
vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group,
2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group,
2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group,
3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group,
2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group,
3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
[0103] Specific examples of the "substituted C2-6 alkenyl group"
include a C2-6 haloalkenyl group such as a 2-chloro-1-propenyl
group, 2-fluoro-1-butenyl group or the like; a C1-6 alkoxy C2-6
alkenyl group such as a 2-n-butoxy-vinyl group, 1-ethoxy-vinyl
group or the like; and the like.
[0104] Examples of the "C2-6 alkynyl group" of X.sup.1 include an
ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group,
2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group,
2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group,
3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group,
2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl
group and the like.
[0105] Specific examples of the "substituted C2-6 alkynyl group"
include a C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl
group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group or the
like; and the like.
[0106] Examples of the "C1-6 alkoxy group" of X.sup.1 include a
methoxy group, ethoxy group, n-propoxy group, n-butoxy group,
n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy
group, s-butoxy group, t-butoxy group, i-hexyloxy group and the
like.
[0107] Specific examples of the "substituted C1-6 alkoxy group"
include a C1-6 haloalkoxy group such as a trifluoromethoxy group,
difluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy
group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group,
2,2,3,4,4,4-hexafluoro-butoxy group, chloromethoxy group,
dichloromethoxy group, trichloromethoxy group or the like;
[0108] a C1-6 alkoxy C1-6 alkoxy group such as a methoxymethoxy
group, methoxyethoxy group or the like;
[0109] a C6-10 aryl C1-6 alkoxy group such as a benzyloxy group,
phenethyloxy group or the like; and
[0110] a C3-8 cycloalkyl C1-6 alkoxy group such as a cyclopropyl
methyloxy group or the like.
[0111] Examples of the "C1-6 alkylcarbonyl group" of X.sup.1
include an acetyl group, propionyl group and the like.
[0112] Specific examples of the "substituted C1-6 alkylcarbonyl
group" include a C1-6 haloalkyl carbonyl group such as a
chloroacetyl group, trifluoroacetyl group, trichloroacetyl group or
the like.
[0113] Examples of the "C1-6 alkoxycarbonyl group" of X.sup.1
include a methoxycarbonyl group, ethoxycarbonyl group,
n-propoxycarbonyl group, i-propoxycarbonyl group, t-butoxycarbonyl
group and the like.
[0114] Specific examples of the "substituted C1-6 alkoxycarbonyl
group" include a C1-6 haloalkoxycarbonyl group such as a
fluoromethoxycarbonyl group, chioromethoxycarbonyl group,
bromomethoxycarbonyl group, difluoromethoxycarbonyl group,
dichloromethoxycarbonyl group, dibromomethoxycarbonyl group,
trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group,
tribromomethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group
or the like;
[0115] a C3-8 cycloalkyl C1-6 alkoxycarbonyl group such as a
cyclopropyl methoxycarbonyl group, cyclobutyl methoxycarbonyl
group, cyclopentyl methoxycarbonyl group, cyclohexyl
methoxycarbonyl group, 2-cyclopropyl ethoxycarbonyl group or the
like; and the like.
[0116] Examples of the "C1-6 alkyl aminocarbonyl group" of X.sup.1
include a methyl aminocarbonyl group, ethyl aminocarbonyl group,
butyl aminocarbonyl group, dimethyl aminocarbonyl group, diethyl
aminocarbonyl group, N-butyl-N-methyl aminocarbonyl group and the
like.
[0117] Examples of the "C1-6 alkyl thio group" of X.sup.1 include a
methyl thio group, ethyl thio group, n-propyl thio group, n-butyl
thio group, n-pentyl thio group, n-hexyl thio group, i-propyl thio
group, i-butyl thio group and the like.
[0118] Specific examples of the "substituted C1-6 alkyl thio group"
include a C1-6 haloalkyl thio group such as a trifluoromethyl thio
group, 2,2,2-trifluoroethyl thio group or the like.
[0119] Examples of the "C1-6 alkyl sulfinyl group" of X.sup.1
include a methyl sulfinyl group, ethyl sulfinyl group, t-butyl
sulfinyl group and the like.
[0120] Specific examples of the "substituted C1-6 alkyl sulfinyl
group" include a C1-6 haloalkyl sulfinyl group such as a
trifluoromethyl sulfinyl group, 2,2,2-trifluoroethyl sulfinyl group
or the like.
[0121] Examples of the "C1-6 alkyl sulfonyl group" of X.sup.1
include a methyl sulfonyl group, ethyl sulfonyl group, t-butyl
sulfonyl group and the like.
[0122] Specific examples of the "substituted C1-6 alkyl sulfonyl
group" include a C1-6 haloalkyl sulfonyl group such as a
trifluoromethyl sulfonyl group, 2,2,2-trifluoroethyl sulfonyl group
or the like.
[0123] Examples of the substituents on the "C1-6 alkyl group",
"C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group",
"C1-6 alkyl carbonyl group", "C1-6 alkoxycarbonyl group", "C1-6
alkyl thio group", "C1-6 alkyl sulfinyl group", "C1-6 alkyl
sulfonyl group" of X.sup.1 include a C1-6 alkoxy group, halogeno
group, cyano group, hydroxy group, C3-8 cycloalkyl group, C6-10
aryl group, 3-6 membered heterocyclyl group and the like.
[0124] Examples of the "C3-8 cycloalkyl group" of X.sup.1 include a
cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl
group, cycloheptyl group and the like.
[0125] The "C6-10 aryl group" of X.sup.1 may be a monocyclic ring
or polycyclic ring. If the polycyclic aryl group has at least one
aromatic ring, the remaining rings may be a saturated alicyclic
ring, an unsaturated alicyclic ring or an aromatic ring.
[0126] Examples of the "C6-10 aryl group" include a phenyl group,
naphthyl group, azulenyl group, indenyl group, indanyl group,
tetralinyl group and the like.
[0127] The "3-6 membered heterocyclyl group" of X.sup.1 is a group
having 1-4 hetetro atoms selected from the group consisting of a
nitrogen atom, oxygen atom and sulfur atom as a constitution atom
of the ring. The heterocyclyl group may be a monoheterocyclyl group
or a polyheterocyclyl group. As long as the polyheterocyclyl group
includes at least one hetero ring, the remaining ring may be a
saturated alicyclic ring, an unsaturated alicyclic ring or an
aromatic ring. Examples of the "3-6 membered heterocyclyl group"
include a 3-6 membered saturated heterocyclyl group, 5-6 membered
heteroaryl group, 5-6 membered partially-unsaturated heterocyclyl
group and the like.
[0128] Examples of the "3-6 membered saturated heterocyclyl group"
include an aziridinyl group, epoxy group, pyrrolidinyl group,
tetrahydrofuranyl group, thiazolidinyl group, piperidyl group,
piperazinyl group, morpholinyl group, dioxolanyl group
(specifically, [1,3]dioxolanyl group), dioxanyl group
(specifically, [1,3]dioxanyl group or [1,4]dioxanyl group) and the
like. Among these examples, 5-6 membered saturated heterocyclyl
group is preferable.
[0129] Examples of the "5 membered heteroaryl group" include a
pyrrolyl group, furyl group, thienyl group, imidazolyl group,
pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group,
isothiazolyl group, triazolyl group (specifically, [1,2,3]triazolyl
group or [1,2,4]triazolyl group), oxadiazolyl group (specifically,
[1,2,4]oxadiazolyl group or [1,3,4]oxadiazolyl group), thiadiazolyl
group, tetrazolyl group and the like.
[0130] Examples of the "6 membered heteroaryl group" include a
pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl
group, triazinyl group and the like.
[0131] The "partially unsaturated 5 membered heterocyclyl group"
include a pyrrolinyl group, imidazolinyl group (dihydroimidazolyl
group), pyrazolinyl group, oxazolinyl group, isoxazolinyl group,
thiazolinyl group and the like.
[0132] The "partially unsaturated 6 membered heterocyclyl group"
include a thiopyranyl group, 2H-pyridine-1-yl group,
4H-pyridine-1-yl group and the like.
[0133] The substituents on the "C3-8 cycloalkyl group", "C6-10 aryl
group" and "3 to 6 membered heterocyclyl group" of X.sup.1 include
a C1-6 alkyl group, C1-6 haloalkyl group, hydroxy group, C1-6
alkoxy group, halogeno group, cyano group, nitro group and the
like.
[0134] Examples of the "substituted amino group" of X.sup.1 include
a C1-6 alkyl substituted amino group such as a methyl amino group,
n-butyl amino group, dimethyl amino group, diethyl amino group or
the like.
[0135] Examples of the "halogeno group" of X.sup.1 include a fluoro
group, chloro group, bromo group, iodo group and the like.
[0136] As X.sup.1, a C1-6 alkyl group, C1-6 haloalkyl group, C1-6
haloalkoxy group, hydroxy C1-6 alkyl group, C1-6 alkoxycarbonyl
group, C1-6 alkyl sulfonyl group, halogeno group, cyano group and
formyl group are preferable, and a C1-6 haloalkyl group is more
preferable.
[0137] n represents a chemically acceptable number of X.sup.1 and
represents an integer of 0 to 4. When n is 2 or more, X.sup.1s may
be the same or different. When B.sup.1, B.sup.2, B.sup.3 and
B.sup.4 represent a carbon atom, namely the compound is represented
by formula (a), n is an integer of 0 to 4. When at least one of
B.sup.1, B.sup.2, B.sup.3 and B.sup.4 represents a nitrogen atom,
namely the compound is represented by formula (b), (c), (e) or (f),
n is an integer of 0 to 3. When B.sup.1 and B.sup.3 represent a
nitrogen atom and B.sup.2 and B.sup.4 represent a carbon atom,
namely the compound is represented by formula (b), n is integer of
0 to 2.
[0138] n is preferably an integer of 0 to 2, more preferably 0 or
1.
[0139] When n is 2 or more, two X.sup.1s may bond together to form
a ring.
[R.sup.1]
[0140] R.sup.1 represents a halogeno group, hydroxy group, cyano
group, substituted C1-6 alkyl group, unsubstituted or substituted
C1-6 alkoxy group, unsubstituted or substituted C1-6 alkyl thio
group, unsubstituted or substituted C1-6 alkyl sulfinyl group,
unsubstituted or substituted C1-6 alkyl sulfonyl group,
unsubstituted or substituted C1-6 alkyl sulfonyloxy group, C1-6
alkyl aminocarbonyl group, C1-6 alkylsulfoximino group or a group
represented by --S(.dbd.O)(.dbd.N--R.sup.a)--R.sup.b.
[0141] In the formula, R.sup.a represents a hydrogen atom, cyano
group, C1-6 alkyl group, or unsubstituted or substituted C1-6 alkyl
carbonyl group, R.sup.b represents a C1-6 alkyl.
[0142] The "halogeno group", "C1-6 alkyl aminocarbonyl group",
"C1-6 alkyl thio group", "C1-6 alkyl sulfinyl group", "C1-6 alkyl
sulfonyl group" and the groups having substituents thereon of
R.sup.1 may be the same as the examples of X.sup.1 listed
above.
[0143] Examples of the "substituted C1-6 alkyl group" of R.sup.1
may be the same as the examples of X.sup.1 listed above, and may
also be a C1-6 alkyl substituted aminocarbonyl C1-6 alkyl group
such as a methyl aminocarbonyl methyl group, dimethyl aminocarbonyl
methyl group or the like.
[0144] Examples of the "unsubstituted or substituted C1-6 alkoxy
group" of R.sup.1 may be the same as the examples of X.sup.1 listed
above, and may also be a C1-6 alkoxy C1-6 alkoxy group such as a
methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group or
the like;
[0145] a C1-6 alkyl thio C1-6 alkoxy group such as a methyl
thiomethoxy group, ethyl thiomethoxy group or the like;
[0146] a C1-6 alkyl sulfinyl C1-6 alkoxy group such as a methyl
sulfinyl methoxy group, ethyl sulfinyl methoxy group or the
like;
[0147] a C1-6 alkyl sulfonyl C1-6 methoxy group such as a methyl
sulfonyl methoxy group, ethyl sulfonyl methoxy group or the
like.
[0148] Examples of the "C1-6 alkyl sulfonyloxy group" of R.sup.1
include a methyl sulfonyloxy group, ethyl sulfonyloxy group,
t-butyl sulfonyloxy group and the like.
[0149] Specific examples the "substituted C1-6 alkyl sulfonyloxy
group" include a C1-6 haloalkyl sulfonyloxy group such as a
trifluoromethyl sulfonyloxy group, 2,2,2-trifluoroethyl sulfonyloxy
group or the like.
[0150] Examples of the "C1-6 alkyl sulfoxyimino group" include a
S,S-dimethyl sulfoxyimino group and the like.
[0151] Examples of the "C1-6 alkyl group", "C1-6 alkyl carbonyl
group" of R.sup.a and R.sup.b in formula
--S(.dbd.O)(.dbd.N--R.sup.a)--R.sup.b are the same as the examples
of X.sup.1 listed above. As the "substituted C1-6 alkyl carbonyl
group" of R.sup.a, C1-6 haloalkyl carbonyl group is preferable.
[0152] As R.sup.1, a halogeno group, hydroxy group, cyano group,
C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 alkoxy C1-6 alkoxy
group, C1-6 alkyl thio C1-6 alkoxy group, C1-6 alkyl sulfinyl C1-6
alkoxy group, C1-6 alkyl sulfonyl C1-6 alkoxy group, C1-6 alkyl
thio group, C1-6 haloalkyl thio group, C1-6 alkyl sulfinyl group,
C1-6 haloalkyl sulfinyl group, C1-6 alkyl sulfonyl group, C1-6
haloalkyl sulfonyl group, C1-6 alkyl sulfonyloxy group, C1-6 alkyl
aminocarbonyl group, C1-6 alkyl sulfoxyimino group and a group
represented by formula --S(.dbd.O)(.dbd.N--R.sup.a)--R.sup.b are
preferable, and a C1-6 alkyl thio group, C1-6 alkyl sulfinyl group
and C1-6 alkyl sulfonyl group are more preferable.
[R.sup.2, m]
[0153] R.sup.2 represents an unsubstituted or substituted C1-6
alkyl group, unsubstituted or substituted C2-6 alkenyl group,
unsubstituted or substituted C2-6 alkynyl group, unsubstituted or
substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or
substituted C1-6 alkoxy group, formyl group, unsubstituted or
substituted C1-6 alkyl carbonyl group, unsubstituted or substituted
C1-6 alkoxycarbonyl group, or unsubstituted or substituted C1-6
alkyl sulfonyl group. R.sup.2 is a substituent bonding with any one
of the two nitrogen atoms on the imidazole ring,
[0154] Examples of the "C1-6 alkyl group", "C2-6 alkenyl group",
"C2-6 alkynyl group", "C3-8 cycloalkyl group", "C1-6 alkoxy group",
"C1-6 alkyl carbonyl group", "C1-6 alkoxycarbonyl group", "C1-6
alkyl sulfonyl group" and the groups having substituent thereon of
R.sup.2 are the same as the examples of X.sup.1 listed above.
[0155] As R.sup.2, a C1-6 alkyl group, C3-8 cycloalkyl group
(preferably a C3-6 cycloalkyl group), C1-6 haloalkyl group, C1-6
alkoxy group and hydroxy group are preferable, and a C1-6 alkyl
group is more preferable.
[0156] m represents a number of the oxide group bonding with the
nitrogen atom which does not bond with R.sup.2 on the imidazole
ring, and represents 0 or 1. m is preferably 0.
[R.sup.3]
[0157] R.sup.3 represents a hydrogen atom, unsubstituted or
substituted C1-6 alkyl group, unsubstituted or substituted C6-10
aryl group, halogeno group, cyano group or nitro group.
[0158] Examples of the "C1-6 alkyl group", "C6-10 aryl group",
"halogeno group" and the groups having substituents thereon of
R.sup.3 are the same as the examples of X.sup.1 listed above.
[0159] As R.sup.3, a hydrogen atom, halogeno group and C1-6 alkyl
group are preferable, and a hydrogen atom is more preferable.
[Ar]
[0160] Ar represents an unsubstituted or substituted C6-10 aryl
group or unsubstituted or substituted 5-10 membered heteroaryl
group.
[0161] Examples of the "C6-10 aryl group" of Ar are the same as the
examples of X.sup.1 listed above.
[0162] Examples of the "5-10 membered heteroaryl group" may be the
same as the examples of 5 membered heteroaryl group and 6 membered
heteroaryl group listed as the examples of X.sup.1, and may also be
a 9 membered heteroaryl group such as an indolyl group, isoindolyl
group, benzofuranyl group, indazolyl group, benzoxazolyl group,
benzisoxazolyl group, benzothiazolyl group, benzisothiazolyl group
or the like; a 10 membered heteroaryl group such as a quinolinyl
group, isoquinolinyl group, cinnolinyl group, phthalazinyl group,
quinazolinyl group, quinoxalinyl group or the like; or the
like.
[0163] As Ar, a phenyl group, thienyl group, pyrazolyl group,
thiazolyl group, pyridyl group, pyrimidyl group, pyridazinyl group
and quinolinyl group are preferable, and a phenyl group is more
preferable.
[0164] Examples of the substituents on the "C6-10 aryl group" and
"5-10 membered heteroaryl group" of Ar include a C1-6 alkyl group,
C1-6 haloalkyl group, hydroxy group, C1-6 alkoxy group, C1-6
haloalkoxy group, C1-6 alkoxy C1-6 haloalkyl group, C1-6 alkoxy
C1-6 alkoxy group, C1-6 alkyl thio group, C1-6 haloalkyl thio
group, C1-6 haloalkyl sulfinyl group, C1-6 haloalkyl sulfonyl
group, C1-6 haloalkyl sulfonyloxy group, unsubstituted or
substituted 5-6 membered heteroaryl group, unsubstituted or
substituted C6-10 aryl group, C1-6 haloalkylene dioxy group,
halogeno group, cyano group, nitro group, amino group,
pentafluorosulfanyl group and the like.
[0165] Examples of the "C1-6 alkyl group, C1-6 haloalkyl group,
C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 alkyl thio group,
C1-6 haloalkyl thio group, C1-6 haloalkyl sulfinyl group, C1-6
haloalkyl sulfonyl group, C1-6 haloalkyl sulfonyloxy group, 5-6
membered heteroaryl group and C6-10 aryl group" as the substituents
on the "C6-10 aryl group" and "5-10 membered heteroaryl group" of
Ar are the same as the examples of X.sup.1 listed above.
[0166] Examples of the "C1-6 alkoxy C1-6 haloalkyl group" include a
methoxydifluoromethyl group,
2,2,2-trifluoro-1-methoxy-1-trifluoromethyl ethyl group,
1,1,1,3,3,3-hexafluoro-2-methoxy-propane-2-yl group and the
like.
[0167] Examples of the "C1-6 haloalkylene dioxy group" include a
difluoromethylene dioxy group (--OCF.sub.2O--), tetrafluoroethylene
dioxy group (--OCF.sub.2CF.sub.2O--) and the like. Examples of the
"C1-6 haloalkylene dioxy group substituted C6-10 aryl group"
include a 2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxyl group,
2,2-difluoro-benzo[1,3]dioxolyl group and the like.
[0168] As the substituents on the "C6-10 aryl group" and "5-10
membered heteroaryl group" of Ar, a C1-6 alkyl group, C1-6
haloalkyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6
alkoxy C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkoxy group, C1-6
alkyl thio group, C1-6 haloalkyl thio group, C1-6 haloalkyl
sulfinyl group, C1-6 haloalkyl sulfonyl group, C1-6 haloalkyl
sulfonyloxy group, unsubstituted or substituted 5-6 membered
heteroaryl group (preferably a C1-6 haloalkyl group), unsubstituted
or substituted C6-10 aryl group (preferably a C1-6 haloalkyl
group), C1-6 haloalkylene dioxy group, halogeno group, cyano group,
nitro group, amino group and pentafluorosulfanyl group are
preferable, and a C1-6 haloalkyl group, C1-6 haloalkoxy group, C1-6
alkyl thio group, C1-6 haloalkyl thio group, C1-6 haloalkyl
sulfonyl group, C1-6 haloalkylene dioxy group, halogeno group,
nitro group and cyano group are more preferable.
[0169] As the number of the substituents on the "C6-10 aryl group"
and "5-10 membered heteroaryl group" of Ar, 0 to 3 are preferable,
and 1 or 2 is more preferable.
[0170] As compound (I), a compound represented by formula (I),
wherein R.sup.2 and R.sup.3 are not adjacent, namely a compound
represented by formula (II) or formula (III) is preferable.
##STR00008##
[0171] [in formula (II), X.sup.1, R.sup.1, R.sup.2, R.sup.3,
B.sup.1, B.sup.2, B.sup.3, B.sup.4, n, m and Ar are as defined in
formula (I).]
[0172] There are no particular limitations on the salt of compound
(I) provided that it is an agriculturally and horticulturally
acceptable salt. Examples of the salt include salts of inorganic
acids such as a hydrochloric acid, sulfuric acid or the like; salts
of organic acids such as an acetic acid, lactic acid or the like;
salts of alkaline metals such as a lithium, sodium, potassium or
the like; salts of alkaline earth metals such as a calcium,
magnesium or the like; salts of transition metals such as an iron,
copper or the like; salts of organic bases such as an ammonia,
triethylamine, tributylamine, pyridine, hydrazine or the like; and
the like.
[0173] The compound (I) or salt thereof is not particularly limited
by the production method thereof. In addition, the salt of compound
(I) may be produced from compound (I) by a well-known method. For
example, compound (I) or salt thereof may be obtained by the
well-known production method described in the working examples
[0174] The diarylimidazole compound of the present invention has a
superior effect for preventing harmful organisms such as various
agricultural pests affecting the plant growth, acari or the
like.
[0175] In addition, the diarylimidazole compound of the present
invention has a high safety because it does not have phytotoxicity
against plants and has a low level of toxicity against fishes or
warm-blooded animals. Therefore, the diarylimidazole compound of
the present invention is useful for an active ingredient of
pesticide or acaricide.
[0176] More over, in recent years, many pests such as diamondback
moths, planthoppers, leafhoppers and aphids have developed a
resistance to the organic phosphorous agents and carbamate agents,
and because of this, the efficacy of the traditional agrochemicals
has become insufficient, new agrochemicals that are effective even
for preventing the resistant strains of pests are desired. The
diarylimidazole compound of the present invention demonstrates
superior efficacy for preventing the sensitive strains of pests,
and also for preventing the various resistant strains of pests and
acaricide-resistant strains of acari.
[0177] The diarylimidazole compound of the present invention has a
superior effect for preventing the external and internal parasites
harmful for humans and animals. More over, the diarylimidazole
compound of the preset invention is a highly safe compound, because
it has a low level of toxicity to the fishes or warm-blooded
animals. Therefore, the diarylimidazle compound of the present
invention is useful as an active ingredient of external and
internal parsite control agent.
[0178] In addition, the diarylimidazole compound of the present
invention is effective for preventing the targeted organisms in any
development stages, for example, acari and insect in the stages of
eggs, nymph, larvae, pupa and adult.
[Harmful Organism Control Agent, Insecticide or Acaricide]
[0179] The harmful organism control agent, insecticide or acaricide
of the present invention include at least one compound of the
diarylimidazole compound of the present invention as an active
ingredient. The amount of the diarylimidazole compound included in
the harmful organism control agent, insecticide or acaricide of the
present invention is not particularly limited as long as it
demonstrates prevention effects against the harmful organisms.
[0180] The harmful organism control agent, insecticide or acaricide
of the present invention are preferably used for crops; green
stuff; edible roots; tuber crops; froot trees; trees of tea,
coffee, cacao or the like; grasses for pastures; grasses for lawns;
plants such as cotton; or the like.
[0181] As for the application to the plants, the harmful organism
control agent, insecticide or acaricide of the present invention
may be applied on any one part of the plants, such as leaf, stem,
stalk, flower, bud, fruit, seed, sprout, root, tuber, tuberous
root, shoot, cutting and the like. In addition, although the plant
varieties for which the harmful organism control agent, insecticide
or acaricide of the present invention is applicable are not
particularly limited, examples of the plant varieties include the
originals, varieties, improved varieties, cultivated varieties,
mutant plants, hydrid plants, genetically-modified plants (GMO) and
the like.
[0182] The harmful organism control agent of the present invention
can be used for preventing various agricultural pests and acari by
seed treatment, foliar spraying, soil application or water surface
application and the like.
[0183] Specific examples of the various agricultural pests and
acari which can be prevented by the harmful organism control agent
of the present invention include the followings.
(1) Butterfly or Moth of Lepidoptera Order
[0184] (a) moth belonging to the Arctiidae family, for example,
Hyphantria cunea, Lemyra imparilis;
[0185] (b) moth belonging to the Bucculatricidae family, for
example, Bucculatrix pyrivorella;
[0186] (c) moth belonging to the Carposinidae family, for example,
Carposina sasakii;
[0187] (d) moth belonging to the Crambidae family, for example,
Diaphania indica and Diaphania nitidalis of Diaphania spp.; for
example, Ostrinia furnacalis, Ostrinia nubilalis and Ostrinia
scapulalis of Ostrinia spp.; Others such as Chilo suppressalis,
Cnaphalocrocis medinalis, Conogethes punctiferalis, Diatraea
grandiosella, Glyphodes pyloalis, Hellula undalis, Parapediasia
teterrella;
[0188] (e) moth belonging to the Gelechiidae family, for example,
Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea
operculella, Sitotroga cerealella;
[0189] (f) moth belonging to the Geometridae family, for example,
Ascotis selenaria;
[0190] (g) moth belonging to the Gracillariidae family, for
example, Caloptilia theivora, Phyllocnistis citrella,
Phyllonorycter ringoniella;
[0191] (h) butterfly belonging to the Hesperiidae family, for
example, Parnara guttata;
[0192] (i) moth belonging to the Lasiocampidae family, for example,
Malacosoma neustria;
[0193] (j) moth belonging to the Lymantriidae family, for example,
Lymantria dispar and Lymantria monacha of Lymantria spp.; Others
such as Euproctis pseudoconspersa, Orgyia thyellina;
[0194] (k) moth belonging to the Lyonetiidae family, for example,
Lyonetia clerkella and Lyonetia prunifoliella malinella of Lyonetia
spp.;
[0195] (l) moth belonging to the Noctuidae family, for example,
Spodoptera depravata, Spodoptera eridania, Spodoptera exigua,
Spodoptera frugiperda, Spodoptera littoralis and Spodoptera litura
of Spodoptera spp.; for example, Autographa gamma and Autographa
nigrisigna of Autographa spp.; for example, Agrotis ipsilon and
Agrotis segetum of Agrotis spp.; for example, Helicoverpa armigera,
Helicoverpa assulta and Helicoverpa zea of Helicoverpa spp.; for
example, Heliothis armigera and Heliothis virescens of Heliothis
spp.; Others such as Aedia leucomelas, Ctenoplusia agnata, Eudocima
tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens,
Panolis japonica, Peridroma saucia, Pseudoplusia includens,
Trichoplusia ni;
[0196] (m) moth belonging to the Nolidae family, for example,
Earias insulana;
[0197] (n) butterfly belonging to the Pieridae family, for example,
Pieris brassicae and Pieris rapae crucivora of Pieris spp.;
[0198] (o) moth belonging to the Plutellidae family, for example,
Acrolepiopsis sapporensis and Acrolepiopsis suzukiella of
Acrolepiopsis spp.; others such as Plutella xylostella;
[0199] (p) moth belonging to the Pyralidae family, for example,
Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella,
Galleria mellonella;
[0200] (q) moth belonging to the Sphingidae, for example, Manduca
quinquemaculata and Manduca sexta of Manduca spp.;
[0201] (r) moth belonging to the Stathmopodidae family, for
example, Stathmopoda masinissa;
[0202] (s) moth belonging to the Tineidae family, for example,
Tinea translucens;
[0203] (t) moth belonging to the Tortricidae family, for example,
Adoxophyes honmai and Adoxophyes orana of Adoxophyes spp.; for
example, Archips breviplicanus and Archips fuscocupreanus Archips
spp.; others such as Choristoneura fumiferana, Cydia pomonella,
Eupoecilia ambiguella, Grapholitha molesta, Homona magnanima,
Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses
phaseoli, Pandemis heparana, Sparganothis pilleriana;
[0204] (u) moth belonging to the Yponomeutidae family, for example,
Argyresthia conjugella.
(2) Pest of Thysanoptera Order
[0205] (a) pest belonging to the Phlaeothripidae family,
forexample, Ponticulothrips diospyrosi;
[0206] (b) pest belonging to the Thripidae family, for example,
Frankliniella intonsa and Frankliniella occidentalis of
Frankliniella spp.; for example, Thrips palmi and Thrips tabaci of
Thrips spp.; others such as Heliothrips haemorrhoidalis,
Scirtothrips dorsalis.
(3) Pest of Hemiptera Order
(A) Archaeorrhyncha Suborder
[0207] (a) pest belonging to the Delphacidae family, for example,
Laodelphax striatella, Nilaparvata lugens, Perkinsiella
saccharicida, Sogatella furcifera.
(B) Clypeorrhyncha suborder
[0208] (a) pest belonging to the Cicadellidae family, for example,
Empoasca fabae, Empoasca nipponica, Empoasca onukii and Empoasca
sakaii of Empoasca spp.; others such as Arboridia apicalis,
Balclutha saltuella, Epiacanthus stramineus, Macrosteles
striifrons, Nephotettix cinctinceps.
(C) Heteroptera Suborder
[0209] (a) pest belonging to the Alydidae family, for example,
Riptortus clavatus;
[0210] (b) pest belonging to the Coreidae family, for example,
Cletus punctiger, Leptocorisa chinensis;
[0211] (c) pest belonging to the Lygaeidae family, for example,
Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus;
[0212] (d) pest belonging to the Miridae family, for example,
Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus,
Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus
caelestialium;
[0213] (e) pest belonging to the Pentatomidae family, for example,
Nezara antennata and Nezara viridula of Nezara spp.; for example,
Eysarcoris aeneus, Eysarcoris lewisi and Eysarcoris ventralis of
Eysarcoris spp.; others such as Dolycoris baccarum, Eurydema
rugosum, Glaucias subpunctatus, Halyomorpha halys, Piezodorus
hybneri, Plautia crossota, Scotinophora lurida;
[0214] (f) pest belonging to the Pyrrhocoridae family, for example,
Dysdercus cingulatus;
[0215] (g) pest belonging to the Rhopalidae family, for example,
Rhopalus msculatus;
[0216] (h) pest belonging to the Scutelleridae family, for example,
Eurygaster integriceps;
[0217] (i) pest belonging to the Tingidae family, for example,
Stephanitis nashi.
(D) Sternorrhyncha suborder
[0218] (a) pest belonging to the Adelgidae family, for example,
Adelges laricis;
[0219] (b) pest belonging to the Aleyrodidae family, for example,
Bemisia argentifolii, Bemisia tabaci of Bemisia spp.; others such
as Aleurocanthus spiniferus, Dialeurodes citri, Trialeurodes
vaporariorum;
[0220] (c) pest belonging to the Aphididae family, for example,
Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis
pomi, Aphis sambuci and Aphis spiraecola of Aphis spp.; for
example, Rhopalosiphum maidis and Rhopalosiphum padi of
Rhopalosiphum spp.; for example, Dysaphis plantaginea and Dysaphis
radicola of Dysaphis spp.; for example, Macrosiphum avenae and
Macrosiphum euphorbiae of Macrosiphum spp.; for example, Myzus
cerasi, Myzus persicae and Myzus varians of Myzus spp.; others such
as Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus
hclichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii,
Hyalopterus pruni, Hyperomyzus lactucae, Lipaphis erysimi, Megoura
viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Phorodon
humuli, Schizaphis graminum, Sitobion avenae, Toxoptera
aurantii;
[0221] (d) pest belong to the Coccidae family, for example,
Ceroplastes ceriferus and Ceroplastes rubens of Ceroplastes
spp.;
[0222] (e) pest belonging to the Diaspididae family, for example,
Pseudaulacaspis pentagona and Pseudaulacaspis prunicola of
Pseudaulacaspis spp.; for example, Unaspis euonymi and Unaspis
yanonensis of Unaspis spp.; others such as Aonidiella aurantii,
Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia
paeoniae;
[0223] (f) pest belonging to the Margarodidae family, for example,
Drosicha corpulenta and Icerya purchasi;
[0224] (g) pest belonging to the Phylloxeridae family, for example,
Viteus vitifolii;
[0225] (h) pest belonging to the Pseudococcidae family, for
example, Planococcus citri and Planococcus kuraunhiae of
Planococcus spp.; others such as Phenacoccus solani, Pseudococcus
comstocki;
[0226] (i) pest belonging to the Psyllidae family, for example,
Psylla mali and Sylla pyrisuga of Psylla spp.; others such as
Diaphorina citri.
(4) Pest of Polyphaga suborder
[0227] (a) pest belonging to the Anobiidae family, for example,
Lasioderma serricorne;
[0228] (b) pest belonging to the Attelabidae family, for example,
Byctiscus betulae, Rhynchites heros;
[0229] (c) pest belonging to the Bostrichidae family, for example,
Lyctus brunneus;
[0230] (d) pest belonging to the Brentidae family, for example,
Cylas fonnicarius;
[0231] (e) pest belonging to the Buprestidae family, for example,
Agrilus sinuatus;
[0232] (f) pest belonging to the Cerambycidae family, for example,
Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris,
Xylotrechus pyrrhoderus;
[0233] (g) pest belonging to the Chrysomelidae family, for example,
Bruchus pisorum and Bruchus rufimanus of Bruchus spp.; for example,
Diabrotica barberi, Diabrotica undecimpunctata and Diabrotica
virgifera of Diabrotica spp.; for example, Phyllotreta nemorum and
Phyllotreta striolata of Phyllotreta spp.; others such as
Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa,
Chaetocnema concinna, Leptinotarsa decemlineata, Oulema oryzae,
Psylliodes angusticollis;
[0234] (h) pest belonging to the Coccinellidae family, for example,
Epilachna varivestis and Epilachna vigintioctopunctata of Epilachna
spp.;
[0235] (i) pest belonging to the Curculionidae family, for example,
Anthonomus grandis and Anthonomus pomorum of Anthonomus spp.; for
example, Sitophilus granaries and Sitophilus zeamais of Sitophilus
spp.; others such as Echinocnemus squameus, Euscepes postfasciatus,
Hylobius abietis, Hypera postica, Lissohoptrus oryzophilus,
Otiorhynchus sulcatus, Sitona lineatus, Sphenophorus venatus;
[0236] (j) pest belonging to the Elateridae family, for example,
Melanotus fortnumi and Melanotus tamsuyensis of Melanotus spp.;
[0237] (k) pest belonging to the Nitidulidae family, for example,
Epuraea domina;
[0238] (l) pest belonging to the Scarabaeidae family, for example,
Anomala cuprea and Anomala rufocuprea of Anomala spp.; others such
as Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha
melolontha, Popillia japonica;
[0239] (m) pest belonging to the Scolytidae family, for example,
Ips typographus;
[0240] (n) pest belonging to the Staphylinidae family, for example,
Paederus fuscipes;
[0241] (o) pest belonging to the Tenebrionidae family, for example,
Tenebrio molitor, Tribolium castaneum;
[0242] (p) pest belonging to the Trogossitidae family, for example,
Tenebroides mauritanicus.
[0243] (5) Pest of Diptera Order
(A) Brachycera Suborder
[0244] (a) pest belonging to the Agromyzidae family, for example,
Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae and
Liriomyza trifolii of Liriomyza spp.; others such as Chromatomyia
horticola, Agromyza oryzae;
[0245] (b) pest belonging to the Anthomyiidae family, for example,
Delia platura, Delia radicum of Delia spp.; others such as Pegomya
cunicularia;
[0246] (c) pest belonging to the Drosophilidae family, for example,
Drosophila melanogaster and Drosophila suzukii of Drosophila
spp.;
[0247] (d) pest belonging to the Ephydridae family, for example,
Hydrellia griseola;
[0248] (e) pest belonging to the Psilidae family, for example,
Psila rosae;
[0249] (f) pest belonging to the Tephritidae family, for example,
Bactrocera cucurbitae and Bactrocera dorsalis of Bactrocera spp.;
for example, Rhagoletis cerasi and Rhagoletis pomonella of
Rhagoletis spp.; others such as Ceratitis capitata, Dacus
oleae.
(B) Nematocera suborder
[0250] (a) pest belonging to the Cecidomyiidae family, for example,
Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor,
Sitodiplosis mosellana.
(6) Pest of Orthoptera Order
[0251] (a) pest belonging to the Acrididae family, for example,
Schistocerca Americana and Schistocerca gregaria of Schistocerca
spp.; others such as Chortoicetes terminifera, Dociostaurus
maroccanus, Locusta migratoria, Locustana pardalina, Nomadacris
septemfasciata, Oxya yezoensis;
[0252] (b) pest belonging to the Gryllidae family, for example,
Acheta domestica, Teleogryllus emma;
[0253] (c) pest belonging to the Gryllotalpidae family, for
example, Gryllotalpa orientalis;
[0254] (d) pest belonging to the Tettigoniidae family, for example,
Tachycines asynamorus.
(7) Acari
[0255] (A) Acaridida of Astigmata order:
[0256] (a) acari belonging to the Acaridae family, for example,
Rhizoglyphus echinopus and Rhizoglyphus robini of Rhizoglyphus
spp.; Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus
putrescentiae and Tyrophagus similis of Tyrophagus spp.; and others
such as Acarus siro, Aleuroglyphus ovatus, Mycetoglyphus
fungivorus;
(B) Actinedida of Prostigmata Order
[0257] (a) acari belonging to the Tetranychidae family, for
example, Bryobia praetiosa and Bryobia rubrioculus of Bryobia spp.;
for example, Eotetranychus asiaticus, Eotetranychus boreus,
Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus
kankitus, Eotetranychus pruni, Eotetranychus shii, Eotetranychus
smithi, Eotetranychus suginamensis and Eotetranychus uncatus of
Eotetranychus spp.; for example, Oligonychus hondoensis,
Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus,
Oligonychus orthius, Oligonychus perseae, ligonychus pustulosus,
Oligonychus shinkajii and Oligonychus ununguis of Oligonychus spp.;
for example, Panonychus citri, Panonychus mori and Panonychus uhni
of Panonychus spp.; for example, Tetranychus cinnabarinus,
Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus,
Tetranychus phaselus, Tetranychus urticae and Tetranychus
viennensis of Tetranychus spp.; for example, Aponychus corpuzae and
Aponychus firmianae of Aponychus spp.; for example, Sasanychus
akitanus and Sasanychus pusillus of Sasanychus spp.; for example,
Shizotetranychus celarius, Shizotetranychus longus,
Shizotetranychus miscanthi, Shizotetranychus recki and
Shizotetranychus schizopus of Shizotetranychus spp.; others such as
Tetranychina harti, Tuckerella pavoniformis, Yezonychus
sapporensis;
[0258] (b) acari belonging to the Tenuipalpidae family, for
example, Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus
phoenicis and Brevipalpus russulus of Brevipalpus spp.; for
example, Tenuipalpus pacificus and Tenuipalpus zhizhilashviliae of
Tenuipalpus spp.; and others such as Dolichotetranychus
floridanus;
[0259] (c) acari belonging to the Eriophyidae family, for example,
Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Aceria
paradianthi, Aceria tiyingi, Aceria tulipae and Aceria zoysiea of
Aceria spp.; for example, Eriophyes chibaensis and Eriophyes
emarginatae of Eriophyes spp.; for example, Aculops lycopersici and
Aculops pelekassi of Aculops spp.; for example, Aculus fockeui,
Aculus schlechtendali, which belong Aculus spp.; and others such as
Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis,
Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus,
Paracalacarus podocarpi, Phyllocotruta citri;
[0260] (d) acari belonging to the Transonemidae family, for
example, Tarsonemus bilobatus and Tarsonemus waitei of Tarsonemus
spp.; others such as Phytonemus pallidus, Polyphagotarsonemus
latus;
[0261] (e) acari belonging to the Penthaleidae family, for example,
Penthaleus erytbrocephalus and Penthaleus major of Penthaleus
spp.;
[0262] The harmful organism control agent, insecticide or acaricide
of the present invention may include an additional ingredient other
than the diarylimidazole compound. Examples of the additional
ingredient include well-known carriers for formulation. In
addition, well-known bactericides, insecticides/acaricides,
nematocides, soil pesticides, plant regulators, synergists,
fertilizers, soil improvers, animal feeds and the like may also be
exemplified as the additional additional ingredient. By adding
these additional ingredients, synergistic effects can be
exhibited.
[0263] Examples of the insecticides/acaricides, nematocides, soil
pesticides, anthelmintic agents and the like are as follow.
(1) Acetylcholine esterase inhibitor:
[0264] (a) Carbamate-based: alanycarb, aldicarb, bendiocarb,
benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,
carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,
isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur,
thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylycarb;
fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, allyxycarb, aminocarb,
bufencarb, cloethocarb, metam-sodium, promecarb;
[0265] (b) Organic phosphorus-based: acephate, azamethiphos,
azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos,
chlorfenvinphos, chlormephos, chlorpyriphos, chlorpyriphos-methyl,
coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,
dicrotophos, dimethoate, dimethylvinfos, disulfoton, EPN, ethion,
ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,
fosthiazete, heptenophos, imicyafos, isofenphos, isocarbophos,
isoxathion, malathion, mecarbam, methamidophos, methidathion,
mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl,
parathion, parathion-methyl, phenthoate, phorate, phosalone,
phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos,
propetamphos, prothiofos, pyraclofos, pyridafenthion, quinalphos,
sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,
thiomethon, triazophos, trichlorfon, vamidothion; bromophos-ethyl,
BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methyl
sulphone, dialifos, dichlofenthion, dioxabenzofos, etrimfos,
fensulfothion, flupyrazofos, fonofos, formothion, fosmethilan,
isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb,
propaphos, prothoate, sulprofos.
(2) GABA-agonistic chloride ion channel antagonist: chlordane,
endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole;
camphechlore, heptachlor, dienochlor. (3) Sodium channel modulator:
acrinathrin, d-cis-trans-allethrin, d-trans allethrin, bifenthrin,
bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin,
cycloprotophosphorus, cycloprothrin, cyfluthrin, .beta.-cyfluthrin,
cyhalothrin, .lamda.-cyhalothrin, .gamma.-cyhalothrin,
cypermethrin, .alpha.-cypermethrin, .beta.-cypermethrin,
.theta.-cypermethrin, .epsilon.-cypermethrin, cyphenothrin
[(1R)-trans isomer], .delta.-methrin, empenthrin
[(EZ)-(1R)-isomer], esfenvalerate, ethofenprox, fenpropathrin,
fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,
halfenprox, imiprothrin, kadethrin, permethrin, phenothrin
[(1R)-trans isomer], prallethrin, pyrethrum, resmethrin,
silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer],
tralomethrin, transfluthrin; allethrin, pyrethrin, pyrethrin I,
pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin,
biopermethrin, transpermethirn, fenfluthrin, fenpirithrin,
flubrocythrinate, flufenoprox, metofluthrin, protrifenbute,
pyresmethrin, terallethrin. (4) Nicotinic acetylcholine receptor
agonist: acetamiprid, clothianidine, dinotefuran, imidacloprid,
nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor,
nicotine, flupyradifurone. (5) Nicotinic acetylcholine receptor
allosteric modulator: spinetoram, spinosad. (6) Chloride channel
activator: abamectin, emamectin benzoate, lepimectin, milbemectin;
ivermectin, seramectin, doramectin, eprinomectin, moxidectin;
milbemycin; milbemycin oxime. (7) Juvenile honnone-like substances:
hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen,
diofenolan, epofeneonane, triprene. (8) Other nonspecific
inhibitor: methyl bromide, chloropierin, sulfuryl fluoride, borax,
tartar emetic. (9) Homoptera selective feeding inhibitor:
flonicamid, pymetrozine, pyrifluquinazon. (10) Acari growth
inhibitor: clofentezine, diflovidazin, hexythiazox, etoxazole. (11)
Microorganism-derived insect midgut inner membrane distrupting
agent: Bacillus thuringiensis subsp. Israelensi, Bacillus
sphaericus, Bacillus thuringiensis subsp. Aizawai, Bacillus
thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp.
Tenebrionis, Bt crop protein: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105,
Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1. (12)
Mitochondria ATP biosynthesis enzyme inhibitor: diafenthiuron,
azocyclotin, cyhexitin, fenbutatin oxide, propargite, tetradifon.
(13) Oxidative phosphorylation uncoupling agent: chlorfenapyr,
sulfluramid, DNOC; binapacryl, dinobuton, dinocap. (14) Nicotinic
acetylcholine receptor channel blocker: bensultap, cartap
hydrochloride; nereistoxin; thiosultap-sodium, thiocyclarm. (15)
Chitin synthesis inhibitor: bistrifluron, chlorfluazuron,
diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron,
lufenuron, novaluron, nobifumuron, teflubenzuron, triflumuron,
buprofezin, fluazuron. (16) Diptera molting disturbing agent:
cyromazine. (17) Molting hormone receptor agonist: chromafenozide,
halofenozide, methoxyfenozide, tebufenozide. (18) Octopamine
receptor agonist: amitraz, demiditraz, chlordimeform. (19)
Mitochondria electron transfer chain complex III inhibitor:
acequinocyl, fluacrypyrim, hydramethylnon. (20) Mitochondria
electron transfer chain complex I inhibitor: fenazaquin,
fenproximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad,
rotenone. (21) Voltage-dependent sodium channel blocker:
indoxacarb, metaflumizone. (22) Acetyl CoA carboxylase inhibitor:
spirodiclofen, spiromesifen, spirotetramat. (23) Mitochondria
electron transfer chain complex IV inhibitor: aluminium phosphide,
calcium phosphide, phosphine, zinc phosphide, cyanide. (24)
Mitochondria electron transfer chain complex II inhibitor:
cyenopyrafen, cyflumetofen, pyflubumide. (25) Ryanodine receptor
modulator: chlorantraniliprole, cyantraniliprole, flubendiamide,
cyclaniliprole, tetraniliprole. (26) Mixed function oxidase
inhibitor compound: piperonyl butoxide. (27) Latrophilin receptor
agonist: depsipeptide, cyclodepsipeptide, 24 membered
cyclodepsipeptide, emodepside. (28) Others (action mechanism is
unknown): azadirachtin, benzoximate, bifenazate, bromopropylate,
quinomethionate, cryolite, dicofol, pyridalyl; benclothiaz, sulfur,
amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate,
benzomate, methaldehyde, chlorobenzilate, chlothiazoben,
dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine,
gossyplure, japonilure, metoxadiazone, oil, potassium oleate,
tetrasul; triarathene; afidopyropen, flometoquin, flufiprole,
fluensulfone, meperfluthrin, tetramcthylfluthrin, tralopyril,
dimefluthrin, methylneodecanamide; fluralaner, afoxolaner,
fluxametamide,
5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2--
(1H-1,2,4-triaz ole-1-yl)benzonitrile (CAS:943137-49-3),
broflanilide, other meta-diamide type. (29) Antiparastic agent:
[0266] (a) benzimidazoles: fenbendazole, albendazole,
triclabendazole, oxibendazole, mebendazole, oxfendazole,
parbendazole, flubendazole; febantel, netobimin, thiophanate;
thiabendazole, cambendazole;
[0267] (b) salicylanilides: closantel, oxyclozanide, rafoxanide,
niclosamide;
[0268] (c) substituted phenols: nitroxinil, nitroscanate;
[0269] (d) pyridines: pyrantel, morantel;
[0270] (e) imidazothiazoles: levamisole, tetramisole;
[0271] (f) tetrahydropyrimidines: praziquantel, epsiprantel;
[0272] (g) other antiparastic agents: cyclodien, riania, clorsulon,
metronidazole, demijitorazu; piperazine, diethyl carbamazine,
dichlorophen, monepantel, tribendimidine, amidantel;
thiacetarsamide, melorsamine, arsenamide.
[0273] Specific examples of the bactericide are as follows.
(1) Nucleic acid biosynthesis inhibitor:
[0274] (a) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M,
furalaxyl, metalaxyl, metalaxyl-M, oxadixyl; clozylacon,
ofurace;
[0275] (b) adenosine deaminase inhibitor: bupirimate, dimethirimol,
ethirimol;
[0276] (c) DNA/RNA synthesis inhibitor: hymexazol, octhilinone;
[0277] (d) DNA topoisomerase II inhibitor: oxophosphoric acid;
(2) karyokinesis inhibitor and cell division inhibitor:
[0278] (a) .beta.-tubulin polymerization inhibitor: benomyl,
carbendazim, chlorfenazole, fuberidazole, thiabendazole;
thiophanate, thiophanate-methyl; diethofencarb; zoxamide;
ethaboxam;
[0279] (b) cell division inhibitor: pencycuron;
[0280] (c) delocalization inhibitor of spectrin-like protein:
fluopicolide;
(3) Respiration inhibitor:
[0281] (a) complex I NADH oxidation-reduction inhibitor:
diflumetorim; tolfenpyrad;
[0282] (b) complex II succinic acid dehydrogenase inhibitor:
benodanil, flutolanil, mepronil; isofetamido, fluopyram; fenfuram,
furmecyclox; carboxin, oxycarboxin; thifluzamide; benzovindiflupyr,
bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen,
penthiopyrad, Sedaxan; boscalid;
[0283] (c) complex III ubiquinol oxidase Qo inhibitor:
azoxystrobin, coumoxystrobin, coumethoxystrobin, enoxastrobin,
flufenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin,
pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin;
dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin;
famoxadone; fluoxastrobin; fenamidone; pyribencarb;
[0284] (d) complex III ubiquinol reductase Qi inhibitor:
cyazofamid; amisulbrom;
[0285] (e) oxidative phosphorylation uncoupling agent: binapacryl,
meptyldinocap, dinocap; fluazinam; ferimzone;
[0286] (f) oxidative phosphorylation inhibitor (ATP synthase
inhibitor): fenthin acetate, fentin chloride, fentin hydroxide;
[0287] (g) ATP production inhibitor: silthiofam;
[0288] (h) complex III cytochromc bel (ubiquinone reductase) Qx
(unknown) inhibitor: ametoctradin;
(4) Amino acid and protein synthesis inhibitor
[0289] (a) methionine biosynthesis inhibitor: andoprim, cyprodinil,
mepanipyrim, pyrimethanil;
[0290] (b) protein synthesis inhibitor: blasticidin-S; kasugamycin;
kasugamycin hydrochloride; streptomycin; oxytetracycline.
(5) Signal transfer inhibitor:
[0291] (a) quinoxyfen, proquinazid;
[0292] (b) MAP/histidine kinase inhibitor in osmotic pressure
signal transfer: fenpiconil, fludioxonil; chlozolimate, iprodionc,
procymidone, vinclozolin;
(6) Lipid and cell membrane synthesis inhibitor:
[0293] (a) phospholipid biosynthesis and methyltransferase
inhibitor: edifenphos, iprobenfos, pyrazophos; isoprothiolane;
[0294] (b) lipid peroxide agent: biphenyl, chloroneb, dichloran,
quintozene, tecnazene, tolclofos-methyl; etridiazole;
[0295] (c) agents affecting cell membrane: iodocarb, propamocarb,
propamocarb hydrochloride, propamocarb-fosetylate, prothiocarb;
[0296] (d) microorganisms disturbing virus cell membrane: Bacillus
subtilis, Bacillus subtilis strain QST713, Bacillus subtilis strain
FZB24, Bacillus subtilis strain MBI600, Bacillus subtilis strain
D747;
[0297] (e) agents disturbing cell membrane: Melaleuca alternifolia
(tea tree) extract.
(7) Cell membrane sterol biosynthesis inhibitor:
[0298] (a) C14 position demethylation inhibitor in sterol
biosynthesis: triforine; pyrifenox, pyrisoxazole; fenarimol,
flurprimidol, nuarimol; imazalil, imazalil-sulphate, oxpoconazole,
pefurazoate, prochloraz, triflumizole, viniconazole; azaconazole,
bitertanol, bromconazole, cyproconazole, diclobutrazol,
difenoconazole, diniconazole, diniconazole-M, epoxyconazole,
etaconazole, fenbuconazole, fluquinconazole, flusilazole,
flutriafol, furconazole, furconazole-cis, hexaconazole,
imibenconazole, ipuconazole, metconazole, myclobutanil,
penconazole, propiconazole, quinconazole, simeconazole,
tebuconazole, tetraconazole, triadimefon, triadimenol,
triticonazole; prothioconazole, voriconazole;
[0299] (b) .DELTA.14 reductase and
.DELTA.8.fwdarw..DELTA.7-isomerase inhibitor in sterol
biosynthesis: aldimorph, dodemorph, dodemorph-acetate,
fenpropimorph, tridemorph, fenpropidine, piperalin;
spiroxamine;
[0300] (c) 3-keto reductase inhibitor in C4 position demethylation
in sterol biosynthesis system: fenhexamid; fenpyrazamine;
[0301] (d) squalene epoxidase inhibitor in sterol biosynthesis
system: pyributicarb; naftifen, terbinafine.
(8) cell wall synthesis inhibitor
[0302] (a) trehalase inhibitor: validamycin;
[0303] (b) chitin synthetase inhibitor: polyoxins, polyoxorim;
[0304] (c) cellulose synthetase inhibitor: dimethomorph, flumorph,
pyrimorph; benthiavalicarb, iprovalicarb, tolprocarb, valifenalate;
mandipropamide;
(9) Melanin biosynthesis inhibitor
[0305] (a) reductase inhibitor in melamin biosynthesis: fthalide;
pyroquilon; tricyclazole;
[0306] (b) anhydrase inhibitor in melanin biosynthesis:
carpropamid; diclocymet; fenoxanil;
(10) Resistance-inducing agent of host plant:
[0307] (a) agents affecting salicylic acid synthetic pathway:
acibenzolar-s-methyl;
[0308] (b) others: probenazole; tiadinil; isotianil; laminarin;
extract liquid of Reynoutria sachalinensis.
(11) agents of which the activity is unknown: cymoxanil,
osetyl-aluminum, phosphoric acid (phosphate), tecloftalam,
triazoxide, flusulfamide, diclomezine, methasulfocarb,
cyflufenamid, metrafenone, pyriofenone, dodine, dodine free base,
flutianil. (12) Agent having multy activities: copper (copper
salt), bordeaux mixture, copper hydroxide, copper naphthalate,
copper oxide, oxychloride copper, copper sulfate, sulfur, sulfur
product, calcium polysulfide; ferbam, mancozeb, maneb, mancopper,
metiram, polycarbamate, propineb, thiram, zineb, ziram; captan,
captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid;
guazatine, iminoctadine acetate, iminoctadine albesilate;
anilazine; dithianon; chinomethionat; fluoroimide. (13) Other
agents: DBEDC, fluor folpet, guazatine acetate, bis
(8-quinolinolato) copper (II), propamidine, chloropicrin,
cyprofuram, agrobacterium, bethoxazin, diphenylamine, methyl
isothiocyanate (MITC), mildew-mycin, capsaicin, curfraneb,
cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat,
difenzoquat-methyl sulfonate, flumetover, fosetyl calcium, fosetyl
sodium, irmamycin, natamycin, nitrothal isopropyl, oxamocarb,
puropamocin sodium, pyrrolnitrin, tebufloquin, tolnifanide,
zarilamide, algophase, amicarthiazol, oxathiapiprolin, metiram
zinc, benthiazole, trichlaamide, uniconazole, mildew-mycin,
oxyfenthiin, picarbutrazox.
[0309] Furthermore, specific examples of the plant growth
regulators are as follows.
[0310] abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea,
forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin,
gibberelline A, gibberelline A4, gibberelline A7, gibberelline A3,
1-methylcyclopropene, N-acetyl aminoethoxyvinyl glycine
(aviglycine), aminooxyacetate, silver nitrate, cobalt chloride,
IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyrate, dichlorprop,
phenothiol, 1-naphthyl acetamide, ethychlozate, cloxyfonac, maleic
acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid,
salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol,
(+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone,
4-oxo-4-(2-phenyl ethyl)aminobutyric acid; ethephon, chlormequat,
mepiquat chloride, benzyl adenine, 5-amino levulinic acid.
[External Parasite Control Agent]
[0311] The eternal parasite control agent of the present invention
includes at least one of the diarylimidazole compound of the
present invention as an active ingredient. The diarylimidazole
compound of the present invention has superior effect for
preventing the external parasites that are harmful for humans and
animals.
[0312] Examples of the external parasite include acari, louse,
flea, mosquito, biting housefly, flesh fly and the like.
[0313] Examples of the host animals to be treated by the external
parasite control agent of the present invention include
warm-blooded animals such as pet animals for example, dogs, cats or
the like; pet birds; domestic animals for example, cows, horses,
pigs, sheep or the like; domestic fowl; and the like. In addition,
honeybees, stag beetles may also be exemplified.
[0314] The external parasites live on the host animals, especially
live inside or upon the warm-blooded animals. More specifically,
the external parasites are parasitic in the back, armpit,
underbelly, inner thigh and the like of the host animals and obtain
nutritional sources such as blood, dandruff from the animals to
live.
[0315] The external parasite control agent of the present invention
can be applied by a known veterinary method (topical, oral,
parenteral or subcutaneous administration). Examples of the method
include orally administering tablets, capsules and foods mixed with
the external parasite control agent to the animals; administering
to the animals by using immersion liquid, suppository or injection
(intramuscular, subcutaneous, intravenous, intraabdominal or the
like); topically administering oily or aqueous liquid preparation
by spraying, pouring on, spotting on or the like; topically
administering by attaching a collar, ear tag or the like made by
molding a mixture obtained by kneading the external parasite
control agent with a resin to the animals; and the like.
[0316] Specific examples of the external parasite able to be
prevented are as follows.
(1) Acari
[0317] Acari belonging to the Dermanyssidae family, acari belonging
to the Macronyssidae family, acari belonging to the Laelapidae
family, acari belonging to the Varroidae family, acari belonging to
the Argasidae family, acari belonging to the Ixodidae family, acari
belonging to the Psoroptidae family, acari belonging to the
Sarcoptidae family, acari belonging to the Knemidokoptidae family,
acari belonging to the Demodixidae family, acari belonging to the
Trombiculidae family, insect-parasitic acari such as
Coleopterophagus berlesei or the like.
(2) Phthiraptera Order
[0318] Louse belonging to the Haematopinidae family, louse
belonging to the Linognathidae family, biting louse belonging to
the Menoponidae family, biting louse belonging to the Philopteridae
family, biting louse belonging to the Trichodectidae family;
(3) Siphonaptera Order
[0319] Flea belonging to the Pulicidae family, for example,
Ctenocephalides canis and Ctenocephalides felis of Ctenocephalides
spp.;
[0320] Flea belonging to the Tungidae family, flea belonging to the
Ceratophyllidae family, flea belonging to the Leptopsyllidae
family;
(4) Hemiptera Order
(5) Harmful Organism of Diptera Order
[0321] Mosquito belonging to the Culicidae family, black fly
belonging to the Simuliidae family, punkie belonging to the
Ceratopogonidae family, fly belonging to the Tabanidae family, fly
belonging to the Muscidae family, glossina belonging to the
Glossinidae family; flesh fly belonging to the Sarcophagidae
family, fly belonging to the Hippoboscidae family, fly belonging to
the Calliphoridae family, fly belonging to the Oestridae
family;
[Internal Parasite Control Agent or Expellent]
[0322] The internal parasite control agent or expellent of the
present invention include at least one selected from the
diarylimidazole compound of the present invention as an active
ingredient.
[0323] The parasites to be prevented by the internal parasite
control agent or expellent of the present invention live in host
animals, especially live inside of the worm-blooded animals or
fishes (internal parasite). Examples of the host animals for which
the parasite control agent or expellent of the present invention is
applicable include worm-blooded animals such as humans, domestic
mammals (for example, cows, horses, pigs, sheep, goats or the
like), experimental animals (for example, mice, rats, merines
unduiculatus or the like), pet animals (for example, hamsters,
guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets or the
like), wild animals and zoo mammals (for example, monkeys, foxes,
deer, buffalos or the like), domestic fowl (for example, turkeys,
ducks, chickens, qualil or the like), pet birds (for example,
pigeon, parrot, magpie, java sparrow, parakeet, bengalee, canary or
the like); fishes such as salmon, trout, Koi or the like; and the
like. By preventing or exterminating the parasites, parasitic
disease carried by parasites can be prevented or treated.
[0324] Examples of the parasites to be prevented or exterminated
are as follows.
(1) Nematode of Enoplida Order
[0325] (a) Dioctophyma renale belonging to the Dioctophymatidae
family, for example, Dioctophyma renale of Dioctophyma spp.;
[0326] (b) Dioctophyma renale belonging to the Soboliphymatidae
family, for example, Soboliphyme abei and Soboliphyme baturini of
Soboliphyme spp.;
(2) Nematode of Enoplida Order
[0327] (a) Trichinella spiralis belonging to the Trichinellidae
family, for example, Trichinella spiralis of Trichinella spp.;
[0328] (b) whipworms belonging to the Trichuridae family, for
example, Capillaria annulata, Capillaria contorta, Capillaria
hepatica, Capillaria perforans, Capillaria plica and Capillaria
suis of Capillaria spp.; Trichuris vulpis, Trichuris discolor,
Trichuris ovis, Trichuris skrjabini and Trichuris suis of Trichuris
spp.;
(3) Nematode of Rhabditida Order
[0329] Strongyloides stercoralis belonging to the Strongyloididae
family, for example, Strongyloides papillosus, Strongyloides
planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides
stercoralis, Strongyloides tumefaciens and Strongyloides ratti of
Strongyloides spp.;
(4) Nematode of Strongylida Order
[0330] Hookworm belonging to the Ancylostomatidae family, for
example, Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma
duodenale and Ancylostoma tubaeforme of Ancylostoma spp.; Uncinaria
stenocephala of Uncinaria spp.; Bunostomum phlebotomum and
Bunostomum trigonocephalum of Bunostomum spp.;
(5) Nematode of Strongylida Order
[0331] (a) Nematode belonging to the Angiostrongylidae family, for
example, Aelurostrongylus abstrusus of Aelurostrongylus spp.;
Angiostrongylus vasorum and Angiostrongylus cantonesis of
Angiostrongylus spp.;
[0332] (b) Nematode belonging to the Crenosomatidae family, for
example, Crenosoma aerophila and Crenosoma vulpis of Crenosoma
spp.;
[0333] (c) Nematode belonging to the Filaroididae family, for
example, Filaroides hirthi and Filaroides osleri of Filaroides
spp.;
[0334] (d) Lung worms belonging to the Metastrongylidae family, for
example, Metastrongylus apri, Metastrongylus asymmetricus,
Metastrongylus pudendotectus and Metastrongylus salmi of
Metastrongylus spp.;
[0335] (e) Gapeworms trachea belonging to the Syngamidae family,
for example, Cyathostoma bronchialis of Cyathostoma spp.; Syngamus
skrjabinomorpha and Syngamus trachea of Syngamus spp.;
(6) Nematode of Strongylida Order
[0336] (a) Nematode belonging to the Molineidae family, for
example, Nematodirus filicollis and Nematodirus spathiger of
Nematodirus spp.;
[0337] (b) Nematode belonging to the Dictyocaulidae family, for
example, Dictyocaulus filarial and Dictyocaulus viviparous of
Dictyocaulus spp.;
[0338] (c) Nematode belonging to the Haemonchidae family, for
example, Haemonchus contortus of Haemonchus spp.; Mecistocirrus
digitatus of Mecistocirrus spp.;
[0339] (d) Nematode belonging to the Haemonchidae family, for
example, Ostertagia ostertagi of Ostertagia spp.;
[0340] (e) Nematode belonging to the Heligmonellidae family, for
example, Nippostrongylus braziliensis of Nippostrongylus spp.;
[0341] (f) Nematode belonging to the Trichostrongylidae family, for
example, Trichostrongylus axei, Trichostrongylus colubriformis and
Trichostrongylus tenuis of Trichostrongylus spp.; Hyostrongylus
rubidus of Hyostrongylus spp.; Obeliscoides cuniculi of
Obeliscoides spp.;
(7) Nematode of Strongylida Order
[0342] (a) Nematode belonging to the Chabertiidae family, for
example, Chabertia ovina of Chabertia spp.; Oesophagostomum
brevicaudatum (pig), Oesophagostomum columbianum, Oesophagostomum
dentatum, Oesophagostomum georgianum (pig), Oesophagostomum
maplestonei, Oesophagostomum quadrispinulatum (pig),
Oesophagostomum radiatum, Oesophagostomum venulosum and
Oesophagostomum watanabei of Oesophagostomum spp.;
[0343] (b) Nematode belonging to the Stephanuridae family, for
example, Stephanurus dentatus of Stephanurus spp.;
[0344] (c) Nematode belonging to the Strongylidae family, for
example, Strongylus asini, Strongylus edentates, Strongylus equinus
and Strongylus vulgaris of Strongylus spp.;
(8) Nematode of the Oxyurida Order
[0345] Nematode belonging to the Oxyuridae family, for example,
Enterobius anthropopitheci and Enterobius vermicularis of
Enterobius spp.; Oxyuris equi of Oxyuris spp.; Passalurus ambiguous
of Passalurus spp.;
(9) Nematode of Ascaridida Order
[0346] (a) Nematode belonging to the Ascaridiidae family, for
example, Ascaridia galli of Ascaridia spp.;
[0347] (b) Nematode belonging to the Heterakidae family, for
example, Heterakis beramporia, Heterakis brevispiculum, Heterakis
gallinarum, Heterakis pusilla and Heterakis putaustralis of
Heterakis spp.;
[0348] (c) Nematode belonging to the Anisakidae family, for
example, Anisakis simplex of Anisakis spp.;
[0349] (d) Nematode belonging to the Ascarididae family, for
example, Ascaris lumbricoides and Ascaris suum of Ascaris spp.;
Parascaris equorum of Parascaris spp.;
[0350] (e) Nematode belonging to the Toxocaridae family, for
example, Toxocara canis, Toxocara leonine, Toxocarasuum, Toxocara
vitulorum and Toxocara cati of Toxocara spp.;
(10) Nematode of Spirurida Order
[0351] (a) Nematode belonging to the Onchocercidae family, for
example, Brugia malayi, Brugia pahangi and Brugia patei of Brugia
spp.; Dipetalonema reconditum of Dipetalonema spp.; Dirofilaria
immitis of Dirofilaria spp.; Filaria oculi of Filaria spp.;
Onchocerca cervicalis, Onchocerca gibsoni and Onchocerca gutturosa
of Onchocerca spp.;
[0352] (b) Nematode belonging to the Setariidae family, for
example, Setaria digitate, Setaria equine, Setaria labiatopapillosa
and Setaria marshalli of Setaria spp.; Wuchereria bancrofti of
Wuchereria spp.;
[0353] (c) Nematode belonging to the Filariidae family, for
example, Parafilaria multipapillosa of Parafilaria spp.;
Stephanofilaria assamensis, Stephanofilaria dedoesi,
Stephanofilaria kaeli, Stephanofilaria okinawaensis and
Stephanofilaria stilesi of Stephanofilaria spp.;
(11) Nematode of Spirurida Order
[0354] (a) Nematode belonging to the Gnathostomatidae family, for
example, Gnathostoma doloresi and Gnathostoma spinigerum of
Gnathostoma spp.;
[0355] (b) Nematode belonging to the Habronematidae family, for
example, Habronema majus, Habronema microstoma and Habronema muscae
of Habronema spp.; Draschia megastoma of Draschia spp.;
[0356] (c) Nematode belonging to the Physalopteridae family, for
example, Physaloptera canis, Physaloptera cesticillata,
Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina,
Physaloptera papilloradiata, Physaloptera praeputialis,
Physaloptera pseudopraerutialis, Physaloptera rara, Physaloptera
sibirica and Physaloptera vulpineus of Physaloptera spp.;
[0357] (d) Nematode belonging to the Gongylonematidae family, for
eample, Gongylonema pulchrum of Gongylonema spp.;
[0358] (e) Nematode belonging to the Spirocercidae family, for
example, Ascarops strongylina of Ascarops spp.;
[0359] (f) Nematode belonging to the Thelaziidae family, for
example, Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis,
Thelazia rhodesi and Thelazia skrjabini of Thelazia spp.;
[Control Agents Against Other Harmful Organisms]
[0360] Other than the above described harmful organisms, the
harmful organism control agent of the present invention also has a
superior effect for preventing the pests having a stinger or venom
to damage humans and animals, pests carrying various pathogens and
pathogenic bacterias, and pests giving unpleasant feelings to
humans (toxic pest, hyginene pest, unpleasant pest).
[0361] Specific examples are as follows.
(1) Pests of Hymenoptera Order
[0362] Bees belonging to the Argidae family, bees belonging to the
Cynipidae family, bees belonging to the Diprionidae family, alis
belonging to the Formicidae family, bees belonging to the
Mutillidae vamily family, bees belonging to the Vespidae
family.
(2) Other Pests
[0363] Blattodea, termite, Araneae, centipede, millipede,
crustacea, Cimex lectularius.
[Preparation Formulation]
[0364] Several examples of the harmful organism control agatent,
insecticide, acaricide, external parasite control agent, or
internal parasite control agent or expellent of the present
invention are shown bellow. However, the additives and the addition
ratios are not limited to the examples and can be modified over a
wide range. The term "part" in the preparation formulation
indicates "part by wight".
[0365] The followings are the preparation formulations for
agricultural and horticultural use and for paddy rice.
(Preparation 1: Wettable Powder)
[0366] 40 parts of the diarylimidazole compound of the present
invention, 53 parts of diatom earth, 4 parts of fatty alcohol
sulfate and 3 parts of alkylnaphthalene sulfonate were uniformly
mixed and finely pulverized to obtain a wettable powder including
40% of active ingredient.
(Preparation 2: Emulsion)
[0367] 30 parts of the diarylimidazole compound of the present
invention, 33 parts of xylene, 30 parts of dimethylformamide and 7
parts of polyoxyethylene alkylaryl ether were mixed and dissolved
to obtain an emulsion including 30% of active ingredient.
(Preparation 3: Granules)
[0368] 5 parts of the diarylimidazole compound of the present
invention, 40 parts of talc, 38 parts of clay, 10 parts of
bentonite and 7 parts of sodum alkylsulfate were uniformely mixed
and cruched, followed by granulating into a granular shape having a
diameter of 0.5 to 1.0 mm to obtain granules containing 5% active
ingredient.
(Preparation 4: Granules)
[0369] 5 parts of the diarylimidazole compound of the present
invention, 73 parts of clay, 20 parts of bentonite, 1 part of
sodium dioctyl sulfosuccinate and 1 part of potassium phosphate
were thoroughly crushed and mixed followed by the addition of
water, mixing well, granulating and drying to obtain granules
containing 5% active ingredient.
(Preparation 5: Suspension)
[0370] 10 parts of the diarylimidazole compound according to the
present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2
parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of
xanthan gum and 73.8 parts of water were mixed and wet-crushed to a
grain size of 3 microns or less to obtain a suspension containing
10% active ingredient.
[0371] The following are the preparation formulations of the
external parasite control atent, or internal parasite control a
agent or expellent.
(Preparation 6: Granulated Powder)
[0372] 5 part of the diarylimidazole compound of the present
invention was dissolved in an organic solvent to obtain a solution,
and sprayed the solution on 94 parts of kaolin and 1 part of white
carbon, followed by evaporating the solvent under reduced pressure.
This kind of granulated powder may be mixed with animal food.
(Preparation 7: Impregnating Agent)
[0373] 0.1-1 parts of the diarylimidazole compound of the present
invention and 99-99.9 parts of peanut oil were uniformely mixed,
and then filter-sterilized by a sterilizing filter after
adjustment.
(Preparation 8: Pour-on Agent)
[0374] 5 parts of the diarylimidazole compound of the present
invention, 10 parts of myristic acid ester and 85 parts of
isopropanol were uniformely mixed to obtain a pour-on agent.
(Preparation 9: Spot-on Agent)
[0375] 10-15 parts of the diarylimidazole compound of the present
invention, 10 parts of palmitic acid ester and 75-80 parts of
isopropanol were uniformely mixed to obtain a spot-on agent.
(Preparation 10: Spray-on Agent)
[0376] 1 part of the diarylimidazole compound of the present
invention, 10 parts of propylene glycol and 89 parts of isopropanol
were uniformely mixed to obtain a spray-on agent.
EXAMPLES
[0377] The following provides Examples to explain the present
invention more specifically. However, the present invention is not
limited to the following examples.
Example 1
Synthesis of
2-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluorom-
ethyl)phenyl)-1H-imidazole (Compound 1-3)
(Step 1)
Synthesis of 2-oxo-2-(4-(trifluoromethyl)phenyl)acetaldehyde
Oxime
##STR00009##
[0379] 30 g (0.44 mol, 3.3 eq) of sodium ethoxide was dissolved in
700 mol of ethanol and cooled to 0.degree. C. 25 g (0.13 mol, 1.0
eq) of p-(trifluoromethyl)acetophenone and 20 ml (d=0.87, 0.15
mmol, 1.1 eq) of isopentyl nitrite were added to the resulting
solution, followed by stirring for 5 hours at room temperature. The
resulting reaction liquid was then concentrated under reduced
pressure and a saturated ammonium chloride aqueous solution was
poured to the resulting residue. After that, the mixture was
extracted with 20%-methanol/dichloromethane and the resulting
organic layer was dried with anhydrous magnesium sulfate and
filtered. The filtrate was concentrated under reduced pressure, and
the residue was purified by silica gel column chromatography to
obtain 15 g of the objective compound (yield: 51%).
[0380] .sup.1H-NMR of the obtained compound is shown below:
[0381] .sup.1H-NMR (400 MHz, CDCl.sub.3): .delta. 8.45 (br s, 1H),
8.14 (m, 2H), 7.98 (s, 1H), 7.72 (m, 2H).
(Step 2)
Synthesis of 1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole
3-oxide
##STR00010##
[0383] 15 g (0.069 mol, 1.0 eq) of
2-oxo-2-(4-(trifluoromethyl)phenyl)acetaldoxime was dissolved in
300 ml of acetic acid followed by stirring at room temperature. 10
g (0.076 mol, 1.1 eq) of 1,3,5-trimethyl hexahydro-1,3,5-triazine
was added to the resulting solution followed by stirring for 3
hours at room temperature. The resulting reaction liquid was then
concentrated under reduced pressure and the obtained crude crystal
was washed with 50%-ethyl acetate/normal hexane to obtain 11 g of
the objected compound (yield: 66%).
[0384] .sup.1H-NMR of the obtained compound is shown below:
[0385] .sup.1H-NMR (400 MHz, CDCl.sub.3): .delta. 8.14 (d, 1H),
7.75 (m, 2H), 7.50 (m, 2H), 7.30 (d, 1H), 3.66 (s, 3H).
(Step 3)
Synthesis of
2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phe-
nyl)-1H-imidazole 3-oxide (Compound 1-5)
##STR00011##
[0387] 1.0 g (4.1 mmol, 1.1 eq) of
1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole 3-oxide, 0.043
g (0.19 mmol, 5 mol %) of palladium acetate, 0.18 g (0.57 mol, 15
mol %) of tri(p-fluorophenyl)phosphine, 0.11 g (1.1 mmol, 30 mol %)
of pivalic acid, and 1.0 g (7.4 mmol, 2.0 eq) of carbonic acid
potassium were added to a reactor, followed by replacing the air
with argon gas. 14 mol of anhydrous acetonitrile solution of 0.90 g
(3.7 mmol, 1.0 eq) of 4-bromo-3-fluorobenzene trifluoride was added
to the resulting mixture, followed by stirring over night at
70.degree. C. The resulting reaction liquid was filtered over
celite and concentrated under reduced pressure. The obtained crude
crystal was washed with diethylether to obtain 1.1 g of the
objective compound (yield: 73%).
[0388] .sup.1H-NMR of the obtained compound is shown below:
[0389] .sup.1H-NMR (400 MHz, CDCl.sub.3): .delta. 8.21 (m, 1H),
7.80 (m, 2H), 7.64 (m, 1H), 7.59 (m, 2H), 7.57 (m, 1H), 7.47 (s,
1H), 3.57 (d, 3H).
(Step 4)
Synthesis of
2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phe-
nyl)-1H-imidazole (Compound 1-4)
##STR00012##
[0391] 1.1 g (2.7 mmol, 1.0 eq) of
2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phe-
nyl)-1H-imidazole 3-oxide was dissolved in 30 ml of acetic acid
followed by stirring at room temperature. 1.5 g (27 mmol, 10 eq) of
electrolytic iron powder was then added to the resulting solution
followed by stirring for 5 hours at 70.degree. C. The resulting
reaction liquid was concentrated under reduced pressure,
neutralized by a saturated aqueous solution of sodium hydrogen
carbonate, followed by filtering over celite. After that, the
resulting mixture was extracted with dichloromethane and the
obtained organic layer was dried by adding anhydrous magnesium
sulfate and filtered. The filtrate was concentrated under reduced
pressure to obtain 0.83 g of the objective compound (yield
83%).
[0392] .sup.1H-NMR of the obtained compound is shown below:
[0393] .sup.1H-NMR (400 MHz, CDCl.sub.3): .delta. 7.84 (m, 1H),
7.74 (m, 2H), 7.61 (m, 1H), 7.58 (m, 1H), 7.51 (m, 1H), 7.35 (s,
1H), 3.61 (d, 3H).
(Step 5)
Synthesis of
2-(2-(ethylsulfanyl)-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluorom-
ethyl)phenyl)-11H-imidazole (Compound 1-7)
##STR00013##
[0395] 0.53 g (1.4 mmol, 1.0 eq) of
2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phe-
nyl)-1H-imidazole was dissolved in 14 ml of N,N-dimethyl formamide
followed by stirring at room temperature. 0.72 g (80%, 6.8 mmol,
5.0 eq) of ethyl mercaptan sodium was then added to the resulting
solution followed by stirring for 1 hour at 100.degree. C. The
resulting reaction liquid was cooled to room temperature followed
by pouring water and extracted with ethyl acetate. The obtained
organic layer was washed with brine, dried by adding anhydrous
magnesium sulfate and filtered. The filtrate was concentrated under
reduced pressure and the obtained residue was purified by silica
gel column chromatography to obtain 0.30 g of the objective
compound (yield: 50%).
[0396] .sup.1H-NMR of the obtained compound is shown below:
[0397] .sup.1H-NMR (400 MHz, CDCl.sub.3): .delta. 7.73 (m, 2H),
7.60 (m, 3H), 7.53 (m, 2H), 7.33 (s, 1H), 3.52 (s, 3H), 2.94 (q,
2H), 1.32 (t, 3H).
(Step 6)
Synthesis of
2-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluorom-
ethyl)phenyl)-1H-imidazole (Compound 1-3)
##STR00014##
[0399] 0.27 g (0.63 mmol, 1.0 eq) of 2-(2-ethyl
sulfanyl-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phenyl-
)-1H-imidazol e was dissolved in 7 ml of chloroform followed by
stirring at 0.degree. C. 0.31 g (70%, 1.3 mmol, 2.0 eq) of
metachloroperbenzoic acid was added to the resulting solution
followed by stirring for 2 hours at 0.degree. C. The resulting
reaction liquid was poured to a mixed solution of saturated aqueous
solution of sodium hydrogen carbonate and saturated aqueous
solution of sodium thiosulfate followed by extracting with
chloroform. The obtained organic layer was washed with brine,
stirred by adding anhydrous magnesium sulfate and filtered. The
filtrate was concentrated under include pressure and the obtained
residue was purified by silica gel column chromatography to obtain
0.15 g of the objective compound (yield: 51%).
[0400] .sup.1H-NMR of the obtained compound is shown below:
[0401] .sup.1H-NMR (400 MHz, CDCl.sub.3): .delta. 8.47 (m, 1H),
8.03 (m, 1H), 7.73 (m, 3H), 7.60 (m, 2H), 3.47 (q, 2H), 3.44 (s,
3H), 1.26 (t, 3H).
[0402] TABLE 1 to TABLE 9 show the compounds of the present
invention produced by the same production process of the
above-described Examples. In addition, the physical properties of
the compounds are shown in the column of "Physical Property". As
the physical properties, property, melting point (m.p.) or
refraction index are shown.
[0403] In addition, in the tables, Ph represents phenyl group, Me
represents methyl group, Et represents ethyl group, .sup.nPr
represents normal propyl group, .sup.iPr represents isopropyl
group, .sup.cPr represents cyclopropyl group, nBu represent normal
butyl group, sBu represents secondary butyl group and tBu
represents tertial butyl group.
[0404] TABLE 1 shows the substituents of the compounds represented
by formula (1).
##STR00015##
TABLE-US-00001 TABLE 1 No. R.sup.1 (X.sup.1)n Ar R.sup.2 R.sup.3 m
Physical Property 1-1 SO.sub.2Et 4-CF.sub.3
5-CF.sub.3-pyridine-2-yl Me H 0 m.p. 145-148.degree. C. 1-2 SEt
4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0 viscous oil 1-3
SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.144-147.degree. C
1-4 F 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p. 126-128.degree. C. 1-5
F 4-CF.sub.3 4-CF.sub.3--Ph Me H 1 m.p. 229-231.degree. C. 1-6 SEt
4-CF.sub.3 4-CF.sub.3--Ph Me Me 0 m.p. 96-101.degree. C. 1-7 SEt
4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p. 111-113.degree. C 1-8 SEt
4-CF.sub.3 3-CF.sub.3--Ph Me H 0 n.sub.D(22.0.degree. C.)1.5454 1-9
SEt 4-CF.sub.3 2-CF.sub.3--Ph Me H 0 viscous oil 1-10 SEt --
4-CF.sub.3--Ph Me H 1 amorphous 1-11 SOEt -- 4-CF.sub.3--Ph Me H 1
m.p.: 194-195.degree. C. 1-12 SO.sub.2Et -- 4-CF.sub.3--Ph Me H 1
m.p.: 131-132.degree. C. 1-13 SEt -- 4-CF.sub.3--Ph Me H 0
n.sub.D(22.2.degree. C.)1.5962 1-14 SOEt -- 4-CF.sub.3--Ph Me H 0
m.p.: 162-164.degree. C. 1-15 SO.sub.2Et -- 4-CF.sub.3--Ph Me H 0
m.p.: 205-208.degree. C. 1-16 SO.sub.2Et 4-CF.sub.3 2-CF.sub.3--Ph
Me H 0 m.p.: 124-125.degree. C. 1-17 SO.sub.2Et 4-CF.sub.3
3-CF.sub.3--Ph Me H 0 m.p.: 165-166.degree. C. 1-18 SOEt 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 m.p.: 154-155.degree. C. 1-19 SEt 4-CF.sub.3
4-Cl--Ph Me H 0 m.p.: 92-94.degree. C. 1-20 SO.sub.2Et 4-CF.sub.3
4-Cl--Ph Me H 0 m.p.: 172-173.degree. C. 1-21 SEt 4-CF.sub.3
4-.sup.tBu--Ph Me H 0 m.p.: 117-118.degree. C. 1-22 SO.sub.2Et
4-CF.sub.3 4-.sup.tBu--Ph Me H 0 m.p.: 201-202.degree. C. 1-23 SEt
4-CF.sub.3 4-CF.sub.3--Ph Et H 0 viscous oil 1-24 SO.sub.2Et
4-CF.sub.3 4-CF.sub.3--Ph Et H 0 m.p.: 109-110.degree. C. 1-25 SEt
4-CF.sub.3 4-CF.sub.3--Ph Me Cl 0 m.p.: 140-142.degree. C. 1-26 SEt
4-.sup.tBu 4-CF.sub.3--Ph Me H 1 m.p.: 200.degree. C. up 1-27 SEt
4-.sup.tBu 4-CF.sub.3--Ph Me H 0 m.p.: 127-129.degree. C. 1-28 SEt
4-CF.sub.3 4-CF.sub.3--Ph Me Br 0 m.p.: 140-141.degree. C. 1-29
SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me Br 0 m.p.: 153-154.degree.
C. 1-30 SO.sub.2Et 4-.sup.tBu 4-CF.sub.3--Ph Me H 0 m.p.:
197-199.degree. C. 1-31 OEt 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
98-101.degree. C. 1-32 SEt 3-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous
oil 1-33 SO.sub.2Et 3-CF.sub.3 4-CF.sub.3--Ph Me H 0 amorphous 1-34
SOEt 3-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.: 183-184.degree. C. 1-35
SO.sub.2Et 4-CF.sub.3 4-OCF.sub.3--Ph Me H 0 m.p.: 140-142.degree.
C. 1-36 SO.sub.2Et 4-CF.sub.3 3,5-Cl.sub.2--Ph Me H 0 m.p.:
130-131.degree. C. 1-37 SO.sub.2Et 4-CF.sub.3 3,5-F.sub.2--Ph Me H
0 m.p.: 127-131.degree. C. 1-38 SO.sub.2Et 4-CF.sub.3
3,5-(CF.sub.3).sub.2--Ph Me H 0 m.p.: 158-162.degree. C. 1-39
SO.sub.2Et 4-CF.sub.3 3,4-Cl.sub.2--Ph Me H 0 m.p.: 150-151.degree.
C. 1-40 SO.sub.2Et 4-CF.sub.3 26-Cl.sub.2--Ph Me H 0 m.p.:
160-162.degree. C. 1-41 SO.sub.2Et 4-CF.sub.3 3-Cl--Ph Me H 0 m.p.:
127-134.degree. C. 1-42 SO.sub.2Et 4-CF.sub.3 4-F--Ph Me H 0 m.p.:
154-156.degree. C. 1-43 SO.sub.2Et 4-CF.sub.3 Ph Me H 0 m.p.:
149-152.degree. C. 1-44 SO.sub.2Et 4-CF.sub.3 4-OMe--Ph Me H 0
m.p.: 170-171.degree. C. 1-45 SO.sub.2Et 4-CF.sub.3 4-Me--Ph Me H 0
m.p.: 180-181.degree. C. 1-46 SO.sub.2Et 4-CF.sub.3
6-CF.sub.3-pyridine-3-yl Me H 0 m.p : 165-167.degree. C. 1-47
SO.sub.2Et 4-CF.sub.3 5-CF.sub.3-pyridine-3-yl Me H 0 m.p.:
126-129.degree. C. 1-48 SO.sub.2Et 4-CF.sub.3
6-CF.sub.3-pyridine-2-yl Me H 0 m.p.: 141-142.degree. C. 1-49
SO.sub.2Et 4-CF.sub.3 2-Cl-pyridine-4-yl Me H 0 m.p.:
162-164.degree. C. 1-50 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me Cl
0 m.p.: 82-85.degree. C. 1-51 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph
.sup.cPr H 0 amorphous 1-52 SO.sub.2Et 4-CF.sub.3 4-NO.sub.2--Ph Me
H 0 m.p.: 170-172.degree. C. 1-53 SO.sub.2Et 4-CF.sub.3 4-NH3--Ph
Me H 0 m.p.: 208-210.degree. C. 1-54 SO.sub.2Et 4-CF.sub.3 4-Br--Ph
Me H 0 m.p.: 192-195.degree. C. 1-55 SO.sub.2Et 4-CF.sub.3 4-Br--Ph
Me Br 0 m.p.: 182-184.degree. C. 1-56 SO.sub.2Et 4-CF.sub.3
3-Cl-5-CF.sub.3- Me H 0 m.p.: 128-129.degree. C. pyridine-2-yl 1-57
SO.sub.2Et 4-CF.sub.3 4-CHF.sub.2O--Ph Me H 0 m.p.: 149-151.degree.
C. 1-58 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3-pyridine-2-yl Me H 0 m.p.:
164-169.degree. C. 1-59 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3-6-(4- Me H
0 m.p.: 206-209.degree. C. CF.sub.3-pyridine-2- yl)pyridine-2-yl
1-60 SO.sub.2Et 4-F 4-CF.sub.3--Ph Me H 0 m.p.: 171-172.degree. C.
1-61 SEt 2-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous oil 1-62
SO.sub.2Et 2-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous oil 1-63 SOEt
2-CF.sub.3 4-CF.sub.3--Ph Me H 0 amorphous 1-64 SEt 4-CF.sub.3
1-CF.sub.3--1H-pyrazol-4-yl Me H 0 m.p.: 120-121.degree. C. 1-65
SO.sub.2Et 4-CF.sub.3 1-CF.sub.3--1H-pyrazol-4-yl Me H 0 m.p.:
177-179.degree. C. 1-66 SO.sub.2Et 4-CF.sub.3 2-F-4-CF.sub.3--Ph Me
H 0 m.p.: 121-126.degree. C. 1-67 SO.sub.2Et 4-CF.sub.3
2-SEt-4-CF.sub.3--Ph Me H 0 m.p.: 171-172.degree. C. 1-68
SO.sub.2Et 4-CF.sub.3 2-SO.sub.2Et-4-CF.sub.3--Ph Me H 0 m.p.:
154-156.degree. C. 1-69 SO.sub.2Et 4-CF.sub.3 2-CN-4-CF.sub.3--Ph
Me H 0 m.p.: 142-144.degree. C. 1-70 SEt 3-CF.sub.3 4-CF.sub.3--Ph
Me H 0 m.p.: 134-136.degree. C. 1-71 SOEt 3-CF.sub.3 4-CF.sub.3--Ph
Me H 0 m.p.: 165-168.degree. C. 1-72 SO.sub.2Et 3-CF.sub.3
4-CF.sub.3--Ph Me H 0 m.p.: 200.degree. C. up 1-73 SO.sub.2Et
4-CF.sub.3 4-CF.sub.3--Ph CF.sub.3 H 0 m.p.: 155-156.degree. C.
1-74 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph C(.sup.2H).sub.3 H 0
m.p.: 138-141.degree. C. 1-75 SEt 4-CF.sub.3 2-Cl-4-CF.sub.3--Ph Me
H 0 m.p.: 126-128.degree. C. 1-76 SO.sub.2Et 4-CF.sub.3
2-Cl-4-CF.sub.3--Ph Me H 0 n.sub.D(19.0.degree. C.)1.5309 1-77
SO.sub.2Et 4-CF.sub.3 4-(perfluoropropan-2-yl)Ph Me H 0 m.p.:
214-217.degree. C. 1-78 SEt 4-CF.sub.3 4-C2F.sub.5--Ph Me H 0 m.p.:
99-101.degree. C. 1-79 SO.sub.2Et 4-CF.sub.3 4-C2F.sub.5--Ph Me H 0
m.p.: 155-157.degree. C. 1-80 SEt 4-CF.sub.3
4-(1,1,1,3,3,3-F.sub.6-2-OMe- Me H 0 n.sub.D(19.8.degree. C.)1.525
propan-2-yl)Ph 1-81 SO.sub.2Et 4-CF.sub.3
4-(1,1,1,3,3,3-F.sub.6-2-OMe- Me H 0 m.p.: 183-185.degree. C.
propan-2-yl)Ph 1-82 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph CHF.sub.2
H 0 m.p.: 133-135.degree. C. 1-83 SO.sub.2Et 4-CF.sub.3
4-SCF.sub.3--Ph Me H 0 m.p.: 140-143.degree. C. 1-84 SO.sub.2Et
4-CF.sub.3 4-SOCF.sub.3--Ph Me H 0 m.p.: 120-122.degree. C. 1-85
SO.sub.2Et 4-CF.sub.3 6-Cl-pyridine-3-yl Me H 0 m.p.:
168-170.degree. C. 1-86 SO.sub.2Et 4-CF.sub.3
2-CF.sub.3-pyrimidin-5-yl Me H 0 m.p.: 170-174.degree. C. 1-87
SO.sub.2Me 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous oil 1-88
SO.sub.2Et 4-CF.sub.3 4-SO.sub.2CF.sub.3--Ph Me H 0 m.p.:
132-134.degree. C. 1-89 SO.sub.2Et 4-CF.sub.3
2,2-F.sub.2-benzo[1,3]dioxol-5-yl Me H 0 m.p.: 106-108.degree. C.
1-90 SO.sub.2Et 4-CF.sub.3 4-(1,1,1,3,3,3-F.sub.6-propan-2-yl)Ph Me
H 0 m.p.: 194-196.degree. C. 1-91 SO.sub.2Et 4-CF.sub.3
4-CF.sub.3CH.sub.2--Ph Me H 0 m.p.: 154-156.degree. C. 1-92
SO.sub.2Et 4-CF.sub.3 6-OCF.sub.3-pyridine-3-yl Me H 0 viscous oil
1-93 SO.sub.2Et 4-CF.sub.3 4-I--Ph Me H 0 m.p.: 233-235.degree. C.
1-94 SO.sub.2Et 4-CF.sub.3 4-OCH.sub.2OMe--Ph Me H 0 m.p.:
129-130.degree. C. 1-95 SO.sub.2Et 4-CF.sub.3
4-OSO.sub.2CF.sub.3--Ph Me H 0 m.p.: 155-156.degree. C. 1-96
SO.sub.2Et 4-CF.sub.3 4-OCH.sub.2CF.sub.3--Ph Me H 0 m.p.:
159-160.degree. C. 1-97 SO.sub.2Et 4-CF.sub.3 4-SF.sub.5--Ph Me H 0
m.p.: 160-163.degree. C. 1-98 SO.sub.2Et 4-CF.sub.3
3-Cl-4-CF.sub.3--Ph Me H 0 m.p.: 124-126.degree. C. 1-99 SO.sub.2Et
4-CF.sub.3 6-C.sub.2F.sub.5-pyridine-3-yl Me H 0 amorphous 1-100
SO.sub.2Et 4-CF.sub.3 4-CN--Ph Me H 0 m.p.: 184-188.degree. C.
1-101 SO.sub.2Et 4-CF.sub.3 3-F-4-CF.sub.3--Ph Me H 0 m.p.:
85-88.degree. C. 1-102 SO.sub.2Et 4-CF.sub.3 3-CN-4-CF.sub.3--Ph Me
H 0 m.p.: 171-173.degree. C. 1-103 OCH.sub.2OMe 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 m.p.: 102-103.degree. C. 1-104 OH 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 m.p.: 217-221.degree. C. 1-105 OCH.sub.2SMe
4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.: 136-138.degree. C. 1-106
OCH.sub.2SOMe 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
160-163.degree. C. 1-107 OCH.sub.2SO.sub.2Me 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 viscous oil 1-108 OCH.sub.2CF, 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 n.sub.D(18.6.degree. C.)1.5098 1-109
OSO.sub.2Me 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 n.sub.D(19.4.degree.
C.)1.5360 1-110 SO.sub.2Et 4-CF.sub.3 6-CF.sub.3-pyridazin-3-yl Me
H 0 m.p.: 222-224.degree. C. 1-111 SO.sub.2Et 4-CF.sub.3
2-F-4-OCF.sub.3--Ph Me H 0 m.p.: 116-119.degree. C. 1-112 SEt
4-CF.sub.3 4-OCF.sub.3--Ph Me H 0 m.p.: 115-116.degree. C. 1-113
SOEt 4-CF.sub.3 4-OCF.sub.3--Ph Me H 0 m.p.: 153-155.degree. C.
1-114 SO.sub.2Et 4-CF.sub.3 3-CF.sub.3-4-Cl--Ph Me H 0 m.p.:
104-109.degree. C. 1-115 SO.sub.2Et 4-CF.sub.3 3-CF.sub.3-4-Cl--Ph
Me 3-CF.sub.3-4- 0 m.p.: 206-209.degree. C. Cl--Ph 1-116 SO.sub.2Et
4-CF.sub.3 4-(4-CF.sub.3--Ph)Ph Me H 0 m.p.: 224-226.degree. C.
1-117 SO.sub.2Et 4-CF.sub.3 thiophen-2-yl Me 1 0 m.p.:
233-234.degree. C. 1-118 SO.sub.2Et 4-CF.sub.3 thiophen-2-yl Me H 0
m.p.: 178-179.degree. C. 1-119 SO.sub.2Et 4-CF.sub.3
4-SC.sub.2F.sub.5--Ph Me H 0 m.p.: 93-95.degree. C. 1-120
SO.sub.2Et 4-CF.sub.3 6-((4-OMe--Ph)CH.sub.2O)- Me H 0 amorphous
pyridine-3-yl 1-121 SO.sub.2Et 4-CF.sub.3 6-Br-pyridine-3-yl Me H 0
m.p.: 198-201.degree. C. 1-122 SO.sub.2Et 4-CF.sub.3
7-F-quinolin-3-yl Me H 0 m.p.: 196-200.degree. C. 1-123 SO.sub.2Et
4-CF.sub.3 4-OCF.sub.2CHF.sub.2--Ph Me H 0 m.p.: 138-141.degree. C.
1-124 SO.sub.2Et 4-CF.sub.3 2,6-Cl.sub.2-4-CF.sub.3 Me H 0 m.p.:
180-182.degree. C. 1-125 SO.sub.2Et 4-CF.sub.3
2,6-Me.sub.2-4-(perfluoropropan- Me H 0 viscous oil 2-yl)Ph
[0405] TABLE 2 shows the substituents of the compound represented
by formula (2).
##STR00016##
TABLE-US-00002 TABLE 2 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m
Physical Property 2-1 SO.sub.2Et 5-CF.sub.3 4-CF.sub.3--Ph Me H 0
m.p.: 97-101.degree. C. 2-2 SEt 5-CF.sub.3 4-CF.sub.3--Ph Me H 0
m.p.: 151-153.degree. C. 2-3 F -- 4-CF.sub.3--Ph Me H 0 m.p.:
213-214.degree. C. 2-4 SEt -- 4-CF.sub.3--Ph Me H 0 m.p.:
145-147.degree. C. 2-5 SO.sub.2Et -- 4-CF.sub.3--Ph Me H 0 m.p.:
133-136.degree. C. 2-6 SO.sub.2Et -- 4-OCF.sub.3--Ph Me H 0
n.sub.D(22.1.degree. C.)1.5629 2-7 SO.sub.2Et --
6-CF.sub.3-pyridine- Me H 0 m.p.: 157-163.degree. C. 3-yl 2-8
SO.sub.2Et -- 4-C.sub.2F.sub.5--Ph Me H 0 m.p.: 145-147.degree. C.
2-9 SO.sub.2Et -- 4-SCF.sub.3--Ph Me H 0 m.p.: 135-137.degree.
C.
[0406] TABLE 3 shows the substituents of the compounds represented
by formula (3).
##STR00017##
TABLE-US-00003 TABLE 3 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m
Physical Property 3-1 SO.sub.2Et -- 4-CF.sub.3--Ph Me H 0
n.sub.D(21.0.degree. C.)1.5452 3-2 SEt -- 4-CF.sub.3--Ph Me H 0
n.sub.D(21.4.degree. C.)1.6008 3-3 F -- 4-CF.sub.3--Ph Me H 1 m.p.
189-193.degree. C. 3-4 F -- 4-CF.sub.3--Ph Me H 0 m.p.
153-155.degree. C.
[0407] TABLE 4 shows the substitutents of the compound represented
by formula (4).
##STR00018##
TABLE-US-00004 TABLE 4 No. R.sup.1 (X.sup.1)n Ar R.sup.2 R.sup.3 m
Physical Property 4-1 SEt 4-CF.sub.3 4-CF.sub.3--Ph OMe H 0 m.p.:
106-109.degree. C. 4-2 SEt 4-CF.sub.3 4-CF.sub.3--Ph OH H 0 m.p.:
245-249.degree. C. 4-3 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me Me 0
m.p.: 195-197.degree. C. 4-4 SEt 4-CF.sub.3 4-CF.sub.3--Ph Me Me 0
m.p.: 147-149.degree. C. 4-5 SEt 4-CF.sub.3 4-CF.sub.3--Ph Me Br 0
m.p.: 153-155.degree. C. 4-6 SEt 4-CF.sub.3 4-CF.sub.3--Ph Me H 0
m.p.: 109-111.degree. C. 4-7 F 4-CF.sub.3 4-CF.sub.3--Ph Me H 0
m.p.: 73-75.degree. C. 4-8 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me
H 0 m.p.: 180-181.degree. C. 4-9 SOEt 4-CF.sub.3 4-CF.sub.3--Ph Me
H 0 m.p.: 138-139.degree. C.
[0408] TABLE 5 shows the substituents of the compounds represented
by formula (5).
##STR00019##
TABLE-US-00005 TABLE 5 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m
Physical Property 5-1 SEt -- 4-CF.sub.3--Ph Me H 0 m.p.
79-84.degree. C.
[0409] TABLE 6 shows the substituents of the compounds represented
by formula (6).
##STR00020##
TABLE-US-00006 TABLE 6 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m
Physical Property 6-1 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me H 0
n.sub.D(22.0.degree. C.)1.529 6-2 F 4-CF.sub.3 4-CF.sub.3--Ph Me H
0 m.p.: 144-145.degree. C. 6-3 SEt 4-CF.sub.3 4-CF.sub.3--Ph Me H 0
m.p.: 118-121.degree. C. 6-4 SO.sub.2Et 4-CF.sub.3
2-F-4-CF.sub.3--Ph Me H 0 m.p.: 140-141.degree. C. 6-5 SEt
4-CF.sub.3 4-OCF.sub.3--Ph Me H 0 m.p.: 92-94.degree. C. 6-6
SO.sub.2Et 4-CF.sub.3 4-OCF.sub.3--Ph Me H 0 viscous oil 6-7
SO.sub.2Et 4-CF.sub.3 4-OCF.sub.3--Ph Me Cl 0 m.p.: 140-142.degree.
C. 6-8 SEt 4-CF.sub.3 6-CF.sub.3-pyridine-3-yl Me H 0 m.p.:
138-139.degree. C. 6-9 SOEt 4-CF.sub.3 6-CF.sub.3-pyridine-3-yl Me
H 0 m.p.:170-172.degree. C. 6-10 SO.sub.2Et 4-CF.sub.3
6-CF.sub.3-pyridine-3-yl Me H 0 n.sub.D(20.1.degree. C.)1.5334 6-11
SO.sub.2Et 4-CF.sub.3 4-C.sub.2F.sub.5--Ph Me H 0
n.sub.D(18.3.degree. C.)1.5183 6-12 SO.sub.2Et 4-OCF.sub.3
4-CF.sub.3--Ph Me H 0 viscous oil 6-13 SO.sub.2Et 4-SO.sub.2Et
4-CF.sub.3--Ph Me H 0 viscous oil 6-14 SO.sub.2Et 4-Cl
4-CF.sub.3--Ph Me H 0 viscous oil 6-15 S.sup.iPr 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 m.p.: 114-116.degree. C. 6-16
SO.sub.2.sup.iPr 4-CF.sub.3 4-CF.sub.3--Ph Me H 0
n.sub.D(20.0.degree. C.)1.5258 6-17 SO.sub.2Et 4-CN 4-CF.sub.3--Ph
Me H 0 m.p.: 192-193.degree. C. 6-18 SO.sub.2Et 4-CF.sub.3
4-SCF.sub.3--Ph Me H 0 viscous oil 6-19 SO.sub.2Et 4-CF.sub.3
2-CF.sub.3-thiazol-5-yl Me H 0 viscous oil 6-20 F 4-CO.sub.2Me
4-CF.sub.3--Ph Me H 0 m.p.: 188-189.degree. C. 6-21 SEt
4-CONMe.sub.2 4-CF.sub.3--Ph Me H 0 m.p.: 116-117.degree. C. 6-22
SO.sub.2Et 4-CONMe.sub.2 4-CF.sub.3--Ph Me H 0 m.p.:
170-173.degree. C. 6-23 SO.sub.2Et 4-Me 4-CF.sub.3--Ph Me H 0 m.p.:
172-175.degree. C. 6-24 SO.sub.2Et 4-CO.sub.2Me 4-CF.sub.3--Ph Me H
0 amorphous 6-25 SO.sub.2Et 4-CO.sub.2.sup.tBu 4-CF.sub.3--Ph Me H
0 viscous oil 6-26 SO.sub.2Et 4-CH.sub.2OH 4-CF.sub.3--Ph Me H 0
m.p.: 184-188.degree. C. 6-27 SO.sub.2Et 4-CHO 4-CF.sub.3--Ph Me H
0 amorphous 6-28 SO.sub.2Et 4-CHF.sub.2 4-CF.sub.3--Ph Me H 0
amorphous 6-29 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me Cl 0
amorphous 6-30 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
110-115.degree. C. 6-31 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me Br
0 m.p.: 210-212.degree. C. 6-32 SO.sub.2Et 4-CF.sub.3
4-CF.sub.3--Ph Me Me 0 m.p.: 157-160.degree. C. 6-33 Cl
2-Cl-4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.: 139-141.degree. C. 6-34
SEt 2-Cl-4-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous oil 6-35
SO.sub.2Et 2-Cl-4-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous oil 6-36
SO.sub.2Et 4-CF.sub.3 5-CF.sub.3-thiophen-2-yl Me H 0 m.p.:
158-159.degree. C. 6-37 CN 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
175-179.degree. C. 6-38 CONMe, 4-CF.sub.3 4-CF.sub.3--Ph Me H 0
n.sub.D(22.1.degree. C.)1.5407 6-39 CONHMe 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 m.p.: 190-193.degree. C. 6-40 SEt 4-CF.sub.3
3-CF.sub.3--Ph Me H 0 m.p.: 127-129.degree. C. 6-41 SO.sub.2Et
4-CF.sub.3 3-CF.sub.3--Ph Me H 0 m.p.: 86-88.degree. C. 6-42 SMe
4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.: 115-117.degree. C. 6-43 SOMe
4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.: 157-159.degree. C. 6-44
SO.sub.2Me 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous oil 6-45
SCH.sub.2CF.sub.3 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
107-110.degree. C. 6-46 SO.sub.2CH.sub.2CF.sub.3 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 m.p.: 142-143.degree. C. 6-47
N.dbd.S(.dbd.O)Me.sub.2 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
154-156.degree. C. 6-48 CONH.sup.sBu 4-CF.sub.3 4-CF.sub.3--Ph Me H
0 m.p.: 85-87.degree. C. 6-49 CON(Me).sup.sBu 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 n.sub.D(21.8.degree. C.)1.5288 6-50 SEt
4-CF.sub.3 4-SF.sub.5--Ph Me H 0 m.p.: 103-105.degree. C. 6-51
SO.sub.2Et 4-CF.sub.3 4-SF.sub.5--Ph Me H 0 n.sub.D(22.8.degree.
C.)1.5238 6-52 SEt 4-CF.sub.3 4-Cl--Ph Me H 0 m.p.: 112-114.degree.
C. 6-53 SO.sub.2Et 4-CF.sub.3 4-Cl--Ph Me H 0 amorphous 6-54 SEt
4-CF.sub.3 3-C1-4-CF.sub.3--Ph Me H 0 viscous oil 6-55 SO.sub.2Et
4-CF.sub.3 3-Cl-4-CF.sub.3--Ph Me H 0 amorphous 6-56 SO.sub.2Et
4-CF.sub.3 4-C.sub.2F.sub.5--Ph Me H 0 amorphous 6-57 SEt
4-CF.sub.3 2,2-F.sub.2-benzo[1,3]dioxol- Me H 0
n.sub.D(23.2.degree. C.)1.5659 5-yl 6-58 SO.sub.2Et 4-CF.sub.3
2,2-F.sub.2-benzo[1,3]dioxol- Me H 0 m.p.: 140-144.degree. C. 5-yl
6-59 S.sup.nPr 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
104-106.degree. C. 6-60 SO2.sup.nPr 4-CF.sub.3 4-CF.sub.3--Ph Me H
0 m.p.: 126-130.degree. C. 6-61 S(.dbd.O)(.dbd.N--CN)Et 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 amorphous 6-62 F 4-CF.sub.3
5-CF.sub.3-pyridine-2-yl Me H 0 m.p.: 111-113.degree. C. 6-63 SEt
4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0 m.p.: 105-107.degree. C.
6-64 SO.sub.2Et 4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0
amorphous 6-65 S(.dbd.O)(.dbd.N--COCF.sub.3)Et 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 viscous oil 6-66 S(.dbd.O)(.dbd.NH)Et
4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.: 138-140.degree. C. 6-67
S(.dbd.O)(.dbd.NMe)Et 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
168-169.degree. C. 6-68 SEt 4-CF.sub.3 3,5-(CF.sub.3).sub.2--Ph Me
3,5-(CF.sub.3).sub.2--Ph 0 viscous oil 6-69 SO.sub.2Et 4-CF.sub.3
3,5-(CF.sub.3).sub.2--Ph Me H 0 viscous oil 6-70 SEt 4-CF.sub.3
4-(perfluoropropan- Me Br 0 m.p.: 105-107.degree. C. 2-yl)Ph 6-71
SOEt 4-CF.sub.3 4-(perfluoropropan- Me H 0 m.p.: 170-171.degree. C.
2-yl)Ph 6-72 SEt 4-CF.sub.3 3,4-Cl.sub.2--Ph Me Br 0 m.p.:
119-120.degree. C. 6-73 SEt 4-CF.sub.3 3,4-Cl.sub.2--Ph Me H 0
viscous oil 6-74 SO.sub.2Et 4-CF.sub.3 3,4-Cl.sub.2--Ph Me H 0
m.p.: 125-126.degree. C. 6-75 F 4-CF.sub.3 4-CN--Ph Me H 0 m.p.:
177-178.degree. C. 6-76 SEt 4-CF.sub.3
6-C.sub.2F.sub.5-pyridine-3-yl Me Br 0 viscous oil 6-77 SEt
4-CF.sub.3 4-CN--Ph Me H 0 m.p.: 130-132.degree. C. 6-78 F
4-CF.sub.3 3-SEt-4-CF.sub.3--Ph Me H 0 m.p.: 160-163.degree. C 6-79
F 4-CF.sub.3 3-SOEt-4-CF.sub.3--Ph Me H 0 m.p.: 130-133.degree. C.
6-80 F 4-CF.sub.3 3-SO.sub.2Et-4-CF.sub.3--Ph Me H 0 m.p.:
141-143.degree. C. 6-81 SEt 4-CF.sub.3 3-SEt-4-CF.sub.3--Ph Me H 0
m.p.: 89-90.degree. C. 6-82 SO.sub.2Et 4-CF.sub.3
3-SOEt-4-CF.sub.3--Ph Me H 0 m.p.: 90-94.degree. C. 6-83 SO.sub.2Et
4-CF.sub.3 3-SO.sub.2Et-4-CF.sub.3--Ph Me H 0 m.p.: 177-180.degree.
C. 6-84 F 4-CF.sub.3 3-NO.sub.2-4-CF.sub.3--Ph Me H 0 m.p.:
99-102.degree. C. 6-85 CH.sub.2CONHMe 4-CF.sub.3 4-CF.sub.3--Ph Me
H 0 m.p.: 150-152.degree. C. 6-86 CH.sub.2CONMe.sub.2 4-CF.sub.3
4-CF.sub.3--Ph Me H 0 viscous oil 6-87 F 4-CF.sub.3
3-NH.sub.2-4-CF.sub.3--Ph Me H 0 m.p.: 158-159.degree. C. 6-88 SEt
4-CF.sub.3 3-NH.sub.3-4-CF.sub.3--Ph Me H 0 m.p.: 130-132.degree.
C. 6-89 SO.sub.2Et 4-CF.sub.3 3-NH.sub.2-4-CF.sub.3--Ph Me H 0
m.p.: 200-202.degree. C. 6-90 SEt 4-CF.sub.3 3-Br-4-CF.sub.3--Ph Me
H 0 m.p.: 116-118.degree. C. 6-91 SO.sub.2Et 4-CF.sub.3
3-Br-4-CF.sub.3--Ph Me H 0 amorphous 6-92 SEt 4-CF.sub.3
4-.sup.nBt-6-C.sub.2F.sub.5-pyridine- Me H 0 m.p.: 110-112.degree.
C. 3-yl 6-93 SEt 4-CF.sub.3 3-Cl-4-OCF.sub.3--Ph Me Br 0 m.p.:
104-105.degree. C. 6-94 SEt 4-CF.sub.3 3-Cl-4-OCF.sub.3--Ph Me H 0
viscous oil 6-95 SOEt 4-CF.sub.3 3-Cl-4-OCF.sub.3--Ph Me H 0
amorphous 6-96 SEt 4-CF.sub.3 2-Cl-4-CF.sub.3--Ph Me Br 0 m.p.:
128-129.degree. C. 6-97 SO.sub.2Et 4-CF.sub.3 4-CN--Ph Me H 0 m.p.:
183-185.degree. C. 6-98 SO.sub.2Et 4-CF.sub.3 4-CHO Me H 0 m.p.:
147-148.degree. C.
[0410] TABLE 7 shows the substituents of the compounds represented
by formula (7).
##STR00021##
TABLE-US-00007 TABLE 7 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m
Physical Property 7-1 SEt 5-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.
123-125.degree. C. 7-2 SO.sub.2Et 5-CF.sub.3 4-CF.sub.3--Ph Me H 0
m.p. 172-173.degree. C.
[0411] TABLE 8 shows the substituents of the compounds represented
by formula (8).
##STR00022##
TABLE-US-00008 TABLE 8 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m
Physical Property 8-1 SEt 6-CF.sub.3 4-CF.sub.3--Ph Me H 0 viscous
oil 8-2 SO.sub.2Et 6-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.
216-218.degree. C.
[0412] TABLE 9 shows the substituents of the compounds represented
by formula (9).
##STR00023##
TABLE-US-00009 TABLE 9 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m
Physical Property 9-1 F 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
153-154.degree. C. 9-2 SEt 4-CF.sub.3 4-CF.sub.3--Ph Me H 0 m.p.:
93-94.degree. C. 9-3 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3--Ph Me H 0
m.p.: 138-140.degree. C.
[0413] TABLE 10 shows .sup.1H-NMR data measured for some compounds
selected from TABLE 1 to TABLE 9. The measuring temperature is
23.degree. C. (*: measuring temperature of 140.degree. C.).
TABLE-US-00010 TABLE 10 Compound No. NMR (.delta. ppm) 1-2
.sup.1H-NMR(400 MHz, CDCl.sub.3): 8.88(m, 1H), 7.94(m, 1H), 7.77(d,
1H), 7.71(s, 1H), 7.61(s, 1H), 7.52(m, 1H), 3.86(s, 3H), 2.94(q,
2H), 1.30(t 3H). 1-9 1H-NMR(400 MHz, CDCl.sub.3): d 7.84(d, 1H),
7.67-7.50(m, 6H), 7.46(d, 1H), 7.18(s, 1H), 3.21(s, 3H), 2.88(q,
2H), 1.29(t, 3H). 1-10 1H-NMR(400 MHz, CDCl.sub.3): d 7.78(d, 2H),
7.61-7.50(m, 5H), 7.43(s, 1H), 7.40(m, 1H), 3.47(s, 1H),
3.00-2.88(m, 1H), 1.29(t, 3H). 1-23 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 7.73(d, 2H), 7.61-7.59(m, 3H), 7.54-7.50(m, 2H),
7.28(s, 1H), 3.94(q, 2H), 2.65(q, 2H), 1.32(t, 3H), 0.97(t, 3H).
1-33 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 7.73(d, 2H), 7.68-7.66(m,
2H), 7.60(d, 2H), 7.46(d, 1H), 7.33(s, 1H), 3.52(s, 3H), 2.97(q,
2H), 1.34(t, 3H). 1-34 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.34(d,
1H), 7.99(dd, 1H), 7.85(d, 1H), 7.74(d, 2H), 7.60(d, 2H), 7.26(s,
1H), 3.48-3.42(m, 5H), 1.26(m, 3H). 1-51 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 848(d, 1H), 8.01(dd, 1H), 7.80(d, 1H), 7.71(m, 4H),
7.23(s, 1H), 3.70(q, 2H), 3.40(m, 1H), 1.31(t, 3H), 0.64(m, 4H).
1-61 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 7.72(d, 2H), 7.61-7.60(m,
3H), 7.57-7.55(m, 2H), 7.36(s, 1H), 3.39(s, 3H), 2.98-2.88(m, 2H),
1.30(t, 3H). 1-62 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.43(d, 1H),
8.13(d, 1H), 7.89(t, 1H), 7.72(d, 2H), 7.60(d, 2H), 7.30(s, 1H),
3.48-3.22(m, 2H), 3.37(s, 3H), 1.21(t, 3H). 1-63 .sup.1H-NMR(400
MHz, CDCl.sub.3): d 8.30(d, 1H), 7.98(m, 1H), 7.91(t, 1H), 7.75(d,
2H), 7.59(d, 2H), 7.27(s, 1H), 3.41(s, 3H), 3.23-2.82(m, 2H),
1.26(t, 3H). 1-87 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.52(d, 1H),
8.04(dd, 1H), 7.75-7.73(m, 3H), 7.60(d, 2H), 7.28(s, 1H), 3.44(s,
3H), 3.30(s, 3H). 1-92 .sup.1H-NMR(400 MHz, CDCl.sub.3): d
8.46-8.45(m, 2H), 8.04(m, 1H), 7.90(m, 1H), 7.73(d, 1H), 7.14(d,
1H), 3.46(q, 2H), 3.42(s, 3H), 1.26(t, 3H). 1-99 .sup.1H-NMR(400
MHz, CDCl.sub.3): d 8.90(d, 1H), 8.47(d, 1H), 8.05(dd, 1H),
8.00(dd, 1H), 7.83(d, 1H), 7.75(d, 1H), 3.48(s, 3H), 3.46(q, 2H),
1.27(t, 3H). 1-107 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 7.76-7.74(m,
3H), 7.64-7.61(m, 2H), 7.56(d, 1H), 7.34(m, 1H), 7.31(s, 1H),
4.96(s, 2H), 3.59(s, 3H), 2.76(s, 3H). 1-120 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.44(d, 1H), 8.00(dd, 1H), 7.66(d, 1H), 7.40-7.36(m,
2H), 7.32(m, 2H), 7.05(s, 1H), 6.90(m, 2H), 6.69(d, 1H), 5.13(s,
2H), 3.80(s, 3H), 3.43(q, 2H), 3.27(s, 3H), 1.24(t, 3H). 1-125
.sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.47(d, 1H), 8.02(dd, 1H),
7.73(d, 1H), 7.39(s, 2H), 7.03(s, 1H), 3.47(q, 2H), 3.09(s, 3H),
1.26(t, 3H). 6-6 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.51(d, 1H),
8.01(dd, 1H), 7.76-7.73(m, 2H), 7.67(d, 2H), 7.35(m, 1H), 7.15(s,
1H), 3.48(s, 3H), 3.07(q, 2H), 1.20(t, 3H). 6-12 .sup.1H-NMR(400
MHz, CDCl.sub.3): d 8.10(d, 1H), 7.84(d, 2H), 7.75(d, 2H), 7.58(m,
2H), 7.14(s, 1H), 3.50(s, 3H), 3.07(q, 2H), 1.20(t, 3H). 6-13
.sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.74(d, 1H), 8.29(dd, 1H),
7.85(d, 2H), 7.78-7.73(m, 3H), 7.20(s, 1H), 3.51(s, 3H), 3.26(q,
2H), 3.08(q, 2H), 1.39(t, 3H), 1.22(t, 3H). 6-14 .sup.1H-NMR(400
MHz, CDCl.sub.3): d 8.23(d, 1H), 8.84(d, 2H), 7.75(d, 2H), 7.72(dd,
1H), 7.45(d, 1H), 7.36(s, 1H), 7.13(s, 1H), 3.48(s, 3H), 3.05(q,
2H), 1.20(t, 3H). 6-18 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.49(m,
1H), 8.00(m, 1H), 7.75(m, 4H), 7.64(m, 1H), 7.15(s, 1H), 3.49(s,
3H), 3.05(q, 2H), 1.19(t, 3H). 6-19 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.50(d, 1H), 8.19(d, 2H), 8.03(dd, 1H), 7.65(d, 1H),
7.17(s, 1H), 7.13(s, 1H), 3.61(s, 3H), 3.05(q, 2H), 1.22(t, 3H).
6-24 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.86(d, 1H), 8.40(dd, 1H),
7.85(d, 2H), 7.75(d, 2H), 7.61(d, 1H), 7.27(s, 1H), 4.02(s, 3H),
3.49(s, 3H), 3.07(q, 2H), 1.20(t, 3H). 6-25 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.78(d, 1H), 8.33(dd, 1H), 7.85(m, 2H), 7.75(m, 2H),
7.57(d, 1H), 7.16(s, 1H), 3.48(s, 3H), 3.06(q, 2H), 1.65(s, 9H),
1.20(t, 3H). 6-27 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 10.20(s, 1H),
8.72(d, 1H), 8.26(dd, 1H), 7.85(m, 2H), 7.76(m, 2H), 7.70(d, 1H),
7.19(s, 1H), 3.51(s, 3H), 3.08(q, 2H), 1.21(t, 3H). 6-28
.sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.38(s, 1H), 7.92(d, 1H),
7.85(d, 2H), 7.76(d, 2H), 7.63(d, 1H), 7.17(s, 1H), 6.81(t, 1H),
3.50(s, 3H), 3.07(q, 2H), 1.20(t, 3H). 6-29 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.52(d, 1H), 8.06(dd, 1H), 7.84(m, 2H), 7.76(m, 2H),
7.68(d, 1H), 3.50(s, 3H), 3.10(q, 2H), 1.23(t, 3H). 6-34
.sup.1H-NMR(400 MHz, CDCl.sub.3): d 7.88(d, 2H), 7.75(d, 2H),
7.54(s, 1H), 7.38(s, 1H), 7.19(s, 1H), 3.50(s, 3H), 2.95(q, 2H),
1.35(t, 3H). 6-35 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.42(d, 1H),
8.09(d, 1H), 7.86(d, 2H), 7.77(d, 2H), 7.16(s, 1H), 3.50(s, 3H),
3.19(q, 2H), 1.28(t, 3H). 6-44 .sup.1H-NMR(400 MHz, CDCl.sub.3): d
8.58(d, 1H), 8.02(dd, 1H), 7.85(d, 2H), 7.76(d, 2H), 7.68(d, 1H),
7.22(s, 1H), 3.50(s, 3H), 3.02(q, 2H). 6-53 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.50(m, 1H), 7.99(m, 1H), 7.67-7.64(m, 3H), 7.48(d,
1H), 7.14(s, 1H), 3.46(s, 3H), 3.07(q, 2H), 1.20(t, 3H). 6-54
.sup.1H-NMR(400 MHz, CDCl.sub.3): d 7.93(s, 1H), 7.81(d, 1H),
7.74(m, 1H), 7.56(s, 1H), 7.48(m, 1H), 7.40(d, 1H), 7.21(s, 1H),
3.57(s, 3H), 2.96(t, 2H), 1.34(t, 3H). 6-55 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.51(m, 1H), 8.01(m, 1H), 7.91(s, 1H), 7.81(d, 1H),
7.71(m, 1H), 7.66(d, 1H), 7.18(s, 1H), 3.51(s, 3H), 3.07(q, 2H),
1.21(t, 3H). 6-56 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.51(m, 1H),
8.01(m, 1H), 7.78(m, 4H), 7.66(d, 1H), 7.17(s, 1H), 3.51(s, 3H),
3.07(q, 2H), 1.21(t, 3H). 6-61 .sup.1H-NMR(400 MHz, CDCl.sub.3): d
8.53(br s, 1H), 8.13(dd, 1H), 7.86-7.76(m, 5H), 7.12(s, 1H),
3.56(br s, 3H), 3.45(m, 2H), 3.07(q, 2H), 1.38(br t, 3H). 6-64
.sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.88(m, 1H), 8.51(m, 1H),
8.39(d, 1H), 8.02(m, 2H), 7.65(d, 1H), 7.21(s, 1H), 3.89(s, 3H),
3.08(q, 2H), 1.22(t, 3H). 6-65 .sup.1H-NMR(400 MHz, DMSO-d6)*: d
8.38(s, 1H), 8.27(d, 1H), 7.96-7.83(m, 5H), 7.33(s, 1H), 3.80(m,
2H), 3.48(s, 3H), 1.28(t, 3H). 6-68 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.26(s, 2H), 8.00(s, 1H), 7.90(s, 2H), 7.65(d, 2H),
7.54(m, 1H), 7.41(d, 1H), 3.54(s, 3H), 3.07-2.93(m, 2H), 1.32(t,
3H). 6-69 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 8.51(d, 1H), 8.19(s,
2H), 8.02(dd, 1H), 7.96(s, 1H), 7.67(d, 1H), 7.20(s, 1H), 3.53(s,
3H), 3.09(q, 2H), 1.23(t, 3H). 6-73 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 7.85(d, 1H), 7.57-7.55(m, 3H), 7.48(dd, 1H), 7.39(d,
1H), 7.18(s, 1H), 3.53(s, 3H), 2.95(q, 2H), 1.34(t, 3H). 6-76
.sup.1H-NMR(400 MHz, CDCl.sub.3): d 9.09(d, 1H), 8.32(dd, 1H),
7.85(dd, 1H), 7.62(s, 1H), 7.55(dd, 1H), 7.45(d, 1H), 3.59(s, 3H),
2.97(q, 2H), 1.33(t, 3H). 6-86 .sup.1H-NMR(400 MHz, CDCl.sub.3): d
7.83(d, 2H), 7.75(d, 2H), 7.65-7.63(m, 2H), 7.12(s, 1H), 3.75(s,
2H), 3.53(s, 3H), 2.94(s, 3H), 2.87(s, 3H). 6-91 .sup.1H-NMR(400
MHz, CDCl.sub.3): d 8.51(s, 1H), 8.12(s, 1H), 8.01(d, 1H), 7.81(d,
1H), 7.76(d, 1H), 7.66(d, 1H), 7.20(s, 1H), 3.51(s, 3H), 3.07(q,
2H), 1.21(t, 3H). 6-94 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 7.88(d,
1H), 7.67(dd, 1H), 7.53(s, 1H), 7.49-7.39(m, 3H), 7.18(s, 1H),
3.54(s, 3H), 2.95(q, 2H), 1.34(t, 3H). 6-97 .sup.1H-NMR(400 MHz,
CDCl.sub.3): d 8.51(d, 1H), 8.01(dd, 1H), 7.84(d, 1H), 7.67-7.63(m,
2H), 7.45(m, 1H), 7.15(s, 1H), 3.49(s, 3H), 3.07(q, 2H), 1.21(t,
3H). 8-1 .sup.1H-NMR(400 MHz, CDCl.sub.3): d 7.86(d, 2H), 7.76(d,
2H), 7.63(d, 1H), 7.45(d, 1H), 7.26(s, 1H), 3.58(s, 3H), 3.23(q,
2H), 1.37(t, 3H).
[Biological Examination]
[0414] The following test examples demonstrate that the
diarylimidazole compound of the present invention (hereinafter, may
be referred to as "the compound of the present invention") is
useful as an active ingredient of harmful organism control agent,
especially as an active ingredient of insecticide. In addition, the
term "part" is based on weight.
(Preparation of Emulsion for Test)
[0415] parts of the compound of the present invention, 93.6 parts
of dimethyl formamide and 1.4 parts of polyoxyethylene alkylaryl
ether were mixed and dissolved to obtain emulsion (I) including 5%
of active ingredient.
(Test Example 1) Efficacy Test Against Pseudaletia Separate
[0416] Emulsion (I) was diluted with water so that the
concentration of the compound of the present invention reaches 125
ppm. Maize leaves were soaked in the diluted liquid for 30 seconds.
Then the maize leaves were put on Petri dishes, followed by
inoculating 5 second-instar larvae of Pseudaletia separate. The
Petri dishes were placed in a temperature-controlled room with a
temperature of 25.degree. C. and humidity of 60%. Mortality was
investigated after 6 days were passed, and the insect mortality
rate was calculated. The test was repeated twice.
[0417] Efficacy test against Pseudaletia separate was carried out
for the compounds shown in TABLE 11. All of the compounds
demonstrated 80% or more of insect mortality rate against
Pseudaletia separate.
TABLE-US-00011 TABLE 11 Compound No. 1-1 1-2 1-3 1-7 1-11 1-14 1-15
1-17 1-18 1-19 1-20 1-23 1-24 1-32 1-33 1-34 1-35 1-36 1-38 1-39
1-42 1-46 1-47 1-48 1-52 1-54 1-56 1-57 1-58 1-60 1-62 1-63 1-64
1-65 1-66 1-67 1-69 1-71 1-74 1-75 1-76 1-77 1-78 1-79 1-81 1-82
1-83 1-84 1-85 1-86 1-87 1-88 1-89 1-90 1-91 1-92 1-93 1-97 1-98
1-99 1-100 1-101 1-102 1-110 1-111 1-112 1-113 1-114 1-119 1-121
1-122 1-123 2-1 2-2 2-4 2-5 2-6 2-7 2-8 2-9 3-2 3-1 6-1 6-3 6-4 6-7
6-10 6-11 6-12 6-13 6-14 6-18 6-19 6-24 6-28 6-31 6-32 6-35 6-36
6-37 6-41 6-43 6-51 6-52 6-53 6-54 6-55 6-56 6-57 6-58 6-63
6-64
(Test Example 2) Efficacy Test Against Spodoptera litura
[0418] Emulsion (1) was diluted with water so that the
concentration of the compound of the present invention reaches 125
ppm. Cabbage leaves were soaked in the diluted liquid for 30
seconds. Then the cabbage leaves were put on Petri dishes, followed
by inoculating 5 second-instar larvae of Spodoptera litura. The
Petri dishes were placed in a temperature-controlled room with a
temperature was 25.degree. C. and humidity of 60%. Mortality was
investigated after 6 days were passed, and the insect mortality
rate was calculated. The test was repeated twice.
[0419] Efficacy test against Spodoptera litura was carried out for
the compounds shown in TABLE 12. All of the compounds demonstrated
80% or more of insect mortality rate against Spodoptera litura.
TABLE-US-00012 TABLE 12 Compound No. 1-1 1-2 1-3 1-7 1-15 1-17 1-18
1-19 1-20 1-24 1-33 1-35 1-36 1-38 1-39 1-42 1-46 1-47 1-54 1-57
1-58 1-69 1-74 1-77 1-79 1-83 1-85 1-87 1-88 1-89 1-90 1-91 1-92
1-97 1-98 1-99 1-100 1-101 1-102 1-110 1-111 1-112 1-113 1-114
1-119 1-121 1-122 2-1 6-1 6-6 6-11 6-18 6-32 6-35 6-36 6-51 6-52
6-53 6-54 6-55 6-56 6-57 6-58 6-63 6-64
(Test Example 3) Efficacy Test Against Plutella xylostella
[0420] Emulsion (I) was diluted with water so that the
concentration of the compound of the present invention reaches 125
ppm. Cabbage leaves were soaked in the diluted liquid for 30
seconds. Then the cabbage leaves were put on Petri dishes, followed
by inoculating 5 second-instar larvae of Plutella xylostella. The
Petri dishes were placed in a temperature-controlled room with a
temperature was 25.degree. C. and humidity of 60%. Mortality was
investigated after 3 days were passed, and the insect mortality
rate was calculated. The test was repeated twice.
[0421] Efficacy test against Plutella xylostella was carried out
for the compounds shown in TABLE 13. All of the compounds
demonstrated 80% or more of mortality rate against Plutella
xylostella.
TABLE-US-00013 TABLE 13 Compound No. 1-1 1-2 1-3 1-7 1-15 1-17 1-18
1-20 1-24 1-33 1-35 1-36 1-38 1-39 1-42 1-46 1-47 1-54 1-57 1-58
1-77 1-79 1-90 2-1 2-2 2-5 3-2 3-1 6-1 6-6 6-11
(Test Example 4) Efficacy Test Against Aphis gossypii
[0422] Cucumber plants were raised in No. 3 pots and the first true
leaves were inoculated with nymphs of Aphis gossypii. Emulsion (I)
was diluted with water so that the concentration of the compound of
the present invention reaches 125 ppm, followed by spraying the
diluted liquid on the cucumber seedlings. The cucumber seedlings
were then placed in a temperature-controlled room with a
temperature of 25.degree. C. and humidity of 60%. Mortality was
investigated after 4 days were passed from the spraying, and the
insect mortality rate of Aphis gossypii was calculated. The test
was repeated twice.
[0423] Efficacy test against Aphis gossypii was carried out for the
compounds shown in TABLE 14. All of the compounds demonstrated 80%
or more of mortality rate against Aphis gossypii.
TABLE-US-00014 TABLE 14 Compound No. 1-3 1-8 1-13 1-14 1-17 1-20
1-24 1-33 1-35 1-39 1-42 1-46 1-47 1-54 1-57 1-58 1-65 1-66 1-69
1-79 1-83 1-84 1-86 1-87 1-88 1-89 1-90 1-91 1-92 1-97 1-98 1-99
1-100 1-101 1-102 1-111 1-114 2-1 2-5 3-2 3-1 5-1 6-1 6-6 6-12 6-14
6-18 6-19 6-24 6-28 6-36 6-41 6-51 6-52 6-53 6-55
(Test Example 5) Efficacy Test Against Bemisia tabaci
[0424] Emulsion (I) was diluted with water so that the
concentration of the compound of the present invention reaches 125
ppm, then the diluted liquid was sprayed on young seedlings of
tomato, followed by air drying. On the day of the spraying, B-type
adult Bemisia tabaci were released to the seedlings so as to lay
eggs. The number of parasitic larvae was calculated after 12 days
were passed from the spraying. The efficacy of the compound was
evaluated by the following equation of prevention rate. The test
was repeated twice.
Prevention rate=[1-(Nt)/(Nc)].times.100
[0425] Nt: number of parasites in spray-treatment area
[0426] Nc: number of parasites in control area
[0427] Efficacy test against Bemisia tabaci was carried out for the
compounds shown in TABLE 15. All of the compounds demonstrated 80%
or more of prevention rate against Bemisia tabaci.
TABLE-US-00015 TABLE 15 Compound No. 1-3 1-66 1-86 1-92 3-2 1-35
1-79 1-87 1-98 3-1 1-65 1-83 1-91 2-1 6-1
(Test Example 6) Efficacy Test Against Tetranychus kanzawai
[0428] Kidney bean plants were raised in No. 3 pots and the primary
leaves were inoculated with 10 adult female Tetranychus kanzawai.
Emulsion (I) was diluted with water so that the concentration of
the compound of the present invention reaches 125 ppm, followed by
spraying the diluted liquid on the kidney bean seedlings. The
kidney bean seedlings were then placed in a temperature-controlled
room with a temperature of 25.degree. C. and humidity of 65%.
Mortality of the adult Tetranychus kanzawai was investigated after
10 days were passed from the spraying, and the insect mortality
rate of Tetranychus kanzawai was calculated. The test was repeated
twice.
[0429] The efficacy test against Tetranychus kanzawai was carried
out for the compounds shown in TABLE 16. All of the compounds
demonstrated 90% or more of mortality rate against Tetranychus
kanzawai.
TABLE-US-00016 TABLE 16 Compound No. 1-4 1-31 1-60 1-109 6-10 9-1
1-9 1-41 1-61 3-4 6-25 1-25 1-46 1-103 6-9 6-62
(Test Example 7) Efficacy Test Against Aphis gossypii (Root-Dipping
Test)
[0430] Cucumber plants raised in No. 3 pots were pulled out from
the pots, then the soil attached to the roots was washed with tap
water, followed by hydrophonic-cultivating the cucumber plants by
soaking the roots in tap water. The cucumber seedlings were
inoculated with nymphs of Aphis gossypii. Emulsion (I) was diluted
with water to obtain a diluted liquid with a concentration of 8 ppm
of the compound of the present invention. The tap water was
replaced with the diluted liquid, and then the
hydrophonic-cultivation was continued in a temperature-controlled
room with a temperature was 25.degree. C. and humidity of 60%.
[0431] After 6 days were passed from the hydrophonic-cultivation in
the diluted liquid, mortality of Aphis gossypii was investigated
and the insect mortality rate was calculated. The test was repeated
twice.
[0432] The efficacy test against Aphis gosspii was carried out for
Compound 3-1, and the insect mortality rate of Compound 3-1 was 80%
or more.
(Test Example 8) Efficacy Test Against Musca domestica
[0433] The compound of the present invention was diluted with
acetone, followed by dropping to 1 g of cube sugar so that the
concentration reaches to 100 ppm. The cube sugar was placed in a
plastic cup and 10 adult female Musca domestica were released
therein, followed by putting the lid on the cup. The cup was kept
at 25.degree. C., the mortality was investigated after 24 hours was
passed from the releasing of Musca domestica and the insect
mortality rate was calculated by the following equation. The test
was repeated twice.
Insect mortality rate (%)=(number of dead insects/number of sample
insects).times.100
[0434] The efficacy test against Musca domestica was carried out
for Compound 1-35. As a result, the insect mortality rate against
the adult female Musca domestica was 100%.
(Test Example 9) Efficacy Test Against Culex pipiens
[0435] Emulsion (I) was diluted with water so that the
concentration of the compound of the present invention reaches 2
ppm to prepare a chemical solution for test. 20 first-instar larvae
of Culex pipiens were released into 100 ml of the chemical solution
for test, then the number of dead insects was calculated after 1
day was passed, and the insect mortality rate was calculated by the
following equation. The test was repeated twice.
Insect mortality rate (%)=(number of dead insects/number of sample
insects).times.100
[0436] The efficacy test against the first-instar larvae of Culex
pipiens was carried out for Compound 1-35. As a result, the insect
mortality rate against the first-instar larvae of Culex pipiens was
100%.
(Test Example 10) Efficacy Test Against Plutella xylostella (Soil
Irrigating Test)
[0437] Emulsion (I) was diluted with water so that the
concentration of the compound of the present invention reaches 500
ppm to prepare a chemical solution for test. 10 ml of the chemical
solution for test was irrigated to the plant feet of bok choy
seedlings (extending period of 7 major leaves) raised in No. 3
pots, followed by keeping them in a warm room with a temperature of
25.degree. C. for 7 days. The bok choy seedlings were placed in a
glass warm room and 300 adult Plutella xylostella were released to
50 bok choy seedlings. After 7 days were passed from releasing the
insects, the number of living larvae of Plutella xylostella
parasitic in the bok choy seedlings was investigated and the
prevention rate was calculated by the following equation. The test
was repeated twice.
Prevention rate=[1-(Nt)/(Nc)].times.100
[0438] Nt: number of parasites in spray-treatment area
[0439] Nc: number of parasites in control area
[0440] The efficacy test against Plutella xylostella was carried
out for Compounds 1-46, 1-47, 1-65, 1-69, 1-85, 1-102, 1-121, 2-5,
3-1, 6-28 and 6-53. As a result, all of the compounds demonstrated
80% or more of prevention rate against Plutella xylostella.
(Test Example 11) Efficacy Test Against Pseudaletia Separate (Seed
Treatment Test)
[0441] 0.1 g of each compound of the present invention was diluted
with 2 ml of acetone to prepare a chemical solutions for test. 10 g
of wheat seeds was added to the chemical solution for test and air
dried, followed by seedling 100 seeds in a planter. After keeping
the planter in a warm room with a temperature of 25.degree. C. for
7 days, 100 first-instar larvae of Pseudaletia separate were
released in the planter. The planter was kept in a war room with a
temperature of 25.degree. C., the number of living Pseudaletia
separate was investigated after 3 days were passed, and the
prevention rate was calculated by the following equation. The test
was repeated twice.
Prevention rate=[1-(Nt)/(Nc)].times.100
[0442] Nt: number of parasites in spray-treatment area
[0443] Nc: number of parasites in control area
[0444] The efficacy test against the first-instar larvae of
Pseudaletia separate was carried out for Compounds 1-47, 1-65,
1-69, 1-102, 2-5 and 6-53. As a result, all of the compounds
demonstrated 80% or more of prevention rate against the
first-instar larvae of Pseudaletia separate.
(Test Example 12) Efficacy Test Against Rhopalosiphum padi (Seed
Treatment Test)
[0445] 0.1 g of each compound of the present invention was diluted
with 2 ml of acetone to prepare chemical solutions for test. 10 g
of wheat seeds was added to the chemical solution for test and air
dried, followed by seedling 100 seeds in a planter. After keeping
the planter in a warm room with a temperature of 25.degree. C. for
7 days, 50 adult Rhopalosiphum padi were released in the planter.
The number of living Rhopalosiphum padi was investigated after 6
days were passed, and the prevention rate was calculated by the
following equation. The test was repeated twice.
Prevention rate=[1-(Nt)/(Nc)].times.100
Nt: number of parasites in spray-treatment area
[0446] Nc: number of parasites in control area
[0447] The efficacy test against Rhopalosiphum padi was carried out
for Compounds 1-47, 1-65, 1-69, 1-102, 2-5 and 6-53. As a result,
all of the compounds demonstrated 80% or more of prevention rate
against Rhopalosiphum padi.
INDUSTRIAL APPLICABILITY
[0448] The diarylimidazole compound or salt thereof according to
the present invention can prevent harmful organisms which are
harmful for agricultural crops and cause the problem of hygiene.
Particularly, the compound or salt thereof can effectively prevent
acaras and insecticides. Furthermore, the compound or salt thereof
can prevent external parasites and internal parasite which are
harmful for humans and animals and thereby useful for industry.
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