1
DESCRIPTION
TITLE OF INVENTION: PYRAZOLE DERIVATIVES AND PESTICIDES
TECHNICAL FIEL5 D
The present invention relates to a pesticide containing pyrazole derivatives and
salts thereof and pesticides containing them as an active ingredient. In the present
invention, a pesticide means an agent for controlling agriculturally, zootechnically or
hygienically noxious arthropods (such as internal and external parasites in and on farm
10 animals or pet mammals and birds and hygienic or annoying home and workplace
insects) as target pests. In the present invention, an agrochemical means an
insecticide, miticide, nematocide, herbicide or fungicide or the like used in the field of
agriculture.
15 BACKGROUND ART
Although pyrazole derivatives are disclosed, for example, in Patent Documents 1
to 9, they do not disclose the pyrazole derivatives of the present invention at all. Their
usefulness as pesticides, especially, as insecticides, miticides or parasticides for
internal or external, mammal or bird parasites is not known at all, either.
20
PRIOR ART DOCUMENT
Patent Document 1: WO2011/128304
Patent Document 2: WO2009/076454
Patent Document 3: WO2008/044767
25 Patent Document 4: US-A-2004-214838
Patent Document 5: JP-A-2003-313103
Patent Document 6: WO99/010350
Patent Document 7: WO97/034893
Patent Document 8: JP-A-63-174905
30 Patent Document 9: JP-A-62-153273
DISCLOSURE OF THE INVENTION
TECHNICAL PROBLEM
With the advance of development of pesticides targeted at various pest insects
35 such as agricultural pest insects, forest pest insects or hygienic pest insects, various
pesticides have been put into practical use.
However, recently, control of pest insects with conventional insecticides or
fungicides has become difficult in more and more cases, as pest insects acquire
resistance to them over many years of their use. Problems of the high toxicity of some
40 conventional pesticides and of the disturbance of the ecosystem by some conventional
pesticides which remain in the environment for a long period are becoming apparent.
Under these circumstances, development of novel pesticides with high pesticidal activity,
low toxicity and low persistence is always expected.
45 SOLUTION TO PROBLEMS
As a result of their extensive studies to accomplish the above object and, the
present inventors found that the novel pyrazole derivative of the present invention
represented by the following formula (I) are very useful compounds which are excellent
2
in pesticidal activities, especially in insecticidal and miticidal activities, and have little
harmful effect on non-target organisms such as mammals, fish and beneficial insects
and accomplished the present invention.
Namely, the present invention relates to the following [1] to [25].
[1] A pyrazole derivative represented by the formula (1)5 :
wherein A1 is -N(-O)m2 or -CR1,
each of R1 and R3 is independently a hydrogen atom, a halogen atom, cyano, nitro, -OH,
-SH, -NH2, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28a, C3-C8 cycloalkyl,
(C3-C8) cycloalkyl optionally substituted with R28a, C2-C6 alkenyl, (C2-C6) alkenyl
10 optionally substituted with R28a, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl optionally
substituted with R28a, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R28a, C1-
C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-
C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylcarbonyl, C3-
C8 cycloalkylcarbonyl, C1-C6 haloalkylcarbonyl, C3-C8 halocycloalkylcarbonyl, C1-C6
15 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C1-C6 alkylaminosulfonyl, di(C1-C6
alkyl)aminosulfonyl, C1-C6 alkylamino or di(C1-C6 alkyl)amino,
R2 is a halogen atom, cyano, nitro, -OH, -SH, -NH2, C1-C6 alkyl, (C1-C6) alkyl optionally
substituted with R28a, C3-C8 cycloalkyl, (C3-C8) cycloalkyl optionally substituted with R28a,
C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R28a, C3-C8 cycloalkenyl, (C3-
20 C8) cycloalkenyl optionally substituted with R28a, C2-C6 alkynyl, (C2-C6) alkynyl optionally
substituted with R28a, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl,
C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl,
C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl, C1-C6 haloalkylcarbonyl, C3-C8
halocycloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C1-C6
25 alkylaminosulfonyl, di(C1-C6 alkyl)aminosulfonyl, C1-C6 alkylamino or di(C1-C6
alkyl)amino, provided that when n is an integer of at least 2, each R2 may be identical
with or different from one another,
R4 is a hydrogen atom, a halogen atom, cyano, nitro, -OH, -SH, -NH2, C1-C6 alkyl, (C1-
C6) alkyl optionally substituted with R28a, C3-C8 cycloalkyl, (C3-C8) cycloalkyl optionally
30 substituted with R28a, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R28a, C3-
C8 cycloalkenyl, (C3-C8) cycloalkenyl optionally substituted with R28a, C2-C6 alkynyl, (C2-
C6) alkynyl optionally substituted with R28a, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6
alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6
haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl,
35 C1-C6 haloalkylcarbonyl, C3-C8 halocycloalkylcarbonyl, C1-C6 alkylamino or di(C1-C6
alkyl)amino,
Ra is a hydrogen atom, cyano, C1-C15 alkyl, (C1-C15) alkyl optionally substituted with R5,
C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R5, C2-C15 alkenyl, (C2-
C15) alkenyl optionally substituted with R5, C3-C12 cycloalkenyl, (C3-C15) cycloalkenyl
A1 N
N
N
R3 N
R4
(R2)n
Ra
Rb
(O)m1
(1)
3
optionally substituted with R5, C2-C12 alkynyl, (C2-C15) alkynyl optionally substituted with
R5, -OR6, -S(O)rR6, -C(O)R7a, -C(O)OR6a, -NR8cR8d, -C(=NR8b)R7a, -S(O)rN(R8a)R8,
phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to
D1-99,
Rb is -S(O)rR6, -C(O)R7, -C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(S)OR6a, -C(S)SR6a5 ,
-C(O)N(R8a)R8, -C(S)N(R8a)R8, -C(O)N(R8b)N(R8a)R8, -C(O)N(R8a)OR6a, -C(=NR8b)OR6a,
-C(=NR8b)SR6a, -C(=NR8b)N(R8a)R8, -C(=NR8b)R7, D1-49, D1-51, D1-53, D1-59, D1-61
or D1-63 or Rb may form =C(Rb2)Rb3 together with Ra,
Rb2 is a hydrogen atom, C1-C15 alkyl or -S(O)rR6,
10 Rb3 is (C1-C15) alkyl optionally substituted with R14, -OR6, -S(O)rR6 or -N(R8b)R8, or Rb3
may form, together with Rb2, a C4-C6 alkylene chain or a C4-C6 alkenylene chain to form
a 5 to 7-membered ring together with the carbon atom attached to Rb3 and Rb2, wherein
the alkylene chain or the alkenylene chain may contain from 1 to 3 oxygen atoms, sulfur
atoms or nitrogen atoms and may optionally be substituted with a halogen atom, a
15 cyano group, a nitro group, C1-C6 alkyl, (C1-C12) alkyl optionally substituted with R14,
-S(O)rR6, -C(O)R7, -C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(S)OR6a, -C(S)SR6a,
-C(O)N(R8a)R8, -C(S)N(R8a)R8, -C(O)N(R8b)N(R8a)R8, -C(O)N(R8a)OR6, -C(=NR8b)OR6a,
-C(=NR8b)SR6a, -C(=NR8b)N(R8a)R8, -C(=NR8b)R7, phenyl, phenyl substituted with (Z)q,
an oxo group, a thioxo group, =NR8b or a C1-C6 alkylidene group,
20 R5 is a halogen atom, cyano, nitro, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally
substituted with R14, -OH, -OR11, -SH, -S(O)rR11, -C(O)R12, -C(O)OR11a, -C(O)SR6a,
-C(S)OR6a, -C(S)SR6a, -C(O)N(R13a)R13, -C(S)N(R13a)R13, -C(=NOH)R12, -C(=NOR11)R12,
-N(R13a)R13, -Si(R9a)(R9b)R9, -P(O)(OR10)2, -P(S)(OR10)2, phenyl, phenyl substituted with
(Z3)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to D1-99,
25 each of R6 and R6a is independently C1-C15 alkyl, (C1-C15) alkyl optionally substituted
with R14, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14, C2-C15
alkenyl, (C2-C15) alkenyl optionally substituted with R14, C3-C15 cycloalkenyl, (C3-C15)
cycloalkenyl optionally substituted with R14, C2-C15 alkynyl, (C2-C15) alkynyl optionally
substituted with R14, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl substituted
30 with (Z)q or D1-1 to D1-99,
R7 is a hydrogen atom, C1-C15 alkyl, (C1-C15) alkyl optionally substituted with R14, C3-C15
cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14, C2-C15 alkenyl, (C2-C15)
alkenyl optionally substituted with R14, C3-C15 cycloalkenyl, (C3-C15) cycloalkenyl
optionally substituted with R14, C2-C15 alkynyl, (C2-C15) alkynyl optionally substituted
35 with R14, -C(O)R12, -C(O)OR11, -C(O)N(R13a)R13, -C(S)N(R13a)R13, -C(=NOH)R12,
-C(=NOR11)R12, -C{=NN(R13a)R13}R12, phenyl, phenyl substituted with (Z)q, naphthyl,
naphthyl substituted with (Z)q or D1-1 to D1-99, or R7 may form, together with Ra, a C2-
C6 alkylene chain or a C2-C6 alkenylene chain containing a double bond to form a 4 to
8-membered ring together with the carbon atom attached to R7 and the nitrogen atom
40 attached to Ra, wherein the alkylene chain or the alkenylene chain may contain one or
two oxygen atoms, sulfur atoms or nitrogen atoms and may optionally be substituted
with a halogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with
R14, -OH,-OR11, -SH, -S(O)rR11, an oxo group, a thioxo group, =NR8b or a C1-C6
alkylidene group,
45 R7a is a hydrogen atom or R6a,
R8 is a hydrogen atom, cyano, R6a, -S(O)rR11, -C(O)R12, -C(O)OR11a, -C(O)N(R13a)R13,
-C(S)N(R13a)R13, -C(=NOH)R12, -C(=NOR11)R12, -S(O)2N(R13a)R13, phenyl, phenyl
substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to D1-99, or R8
4
may form, together with R8a, a C2-C7 alkylene chain to form a 3 to 8-membered ring
together with the nitrogen atom attached to R8 and R8a, wherein the alkylene chain may
contain an oxygen atom, a sulfur atom or a nitrogen atom and may optionally be
substituted with a halogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl optionally substituted
with R14, phenyl, phenyl substituted with (Z)q, an oxo group or a thioxo group, or R8 5 may
form =C(R8f)R8e together with R8a,
R8a is a hydrogen atom, cyano, C1-C15 alkyl, (C1-C15) alkyl optionally substituted with
R14a, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14a, C2-C15
alkenyl, (C2-C15) alke or nyl optionally substituted with R14a, C3-C15 cycloalkenyl, (C3-
10 C15) cycloalkenyl optionally substituted with R14a, C2-C15 alkynyl or (C2-C15) alkynyl
optionally substituted with R14a, or R8a may form, together with Ra, a C2-C5 alkylene
chain to form a 5 to 8-membered ring together with the nitrogen atom attached to R8a
and the nitrogen atom attached to Ra, wherein the alkylene chain may contain an
oxygen atom, a sulfur atom or a nitrogen atom and may optionally be substituted with a
15 halogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14,
-OH,-OR11, -SH, -S(O)rR11, an oxo group, a thioxo group or =NR8b,
R8b is a hydrogen atom, cyano, nitro, C1-C15 alkyl, (C1-C15) alkyl optionally substituted
with R14, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14, C2-C15
alkenyl, (C2-C15) alkenyl optionally substituted with R14, C3-C15 cycloalkenyl, (C3-C15)
20 cycloalkenyl optionally substituted with R14, C2-C15 alkynyl, (C2-C15) alkynyl optionally
substituted with R14, -OR11, -S(O)rR11, -C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13,
-C(S)N(R13a)R13 or -S(O)2N(R13a)R13,
each of R8c and R8d is independently a hydrogen atom, C1-C6 alkyl, -S(O)rR11
-C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13 or -C(S)N(R13a)R13,
25 R8e is a hydrogen atom, C1-C15 alkyl or -S(O)rR11,
R8f is C1-C15 alkyl, (C1-C15) alkyl optionally substituted with R14, -OR11, -S(O)rR11,
-N(R13a)R13, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q
or or D1-1 to D1-99,
each of R9, R9a and R9b is independently C1-C6 alkyl,
30 R10 is a hydrogen atom or C1-C6 alkyl,
each of R11 and R11a is independently C1-C6 alkyl, (C1-C6) alkyl optionally substituted
with R14a, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R14a, C3-C8
cycloalkenyl, (C3-C8) cycloalkenyl optionally substituted with R14a, C2-C6 alkynyl, (C2-C6)
alkynyl optionally substituted with R14a, C3-C8 cycloalkyl, (C3-C8) cycloalkyl optionally
35 substituted with R14a, -Si(R9a)(R9b)R9, phenyl, phenyl substituted with (Z)q, naphthyl,
naphthyl substituted with (Z)q or or D1-1 to D1-99,
R12 is a hydrogen atom, R11a, -C(O)R16, -C(=NOH)R16, -C(=NOR15)R16, phenyl, phenyl
substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or or D1-1 to D1-99,
each of R13 and R13a is independently a hydrogen atom, R11a, -S(O)rR15, -C(O)OR15a,
40 -C(O)R16, -C(O)N(R17a)R17, -C(S)N(R17a)R17, -S(O)2N(R17a)R17, phenyl, phenyl
substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or or D1-1 to D1-99, or R13
and R13a may form, together with each other, a C2-C7 alkylene chain to form a 3 to 8-
membered ring together with the nitrogen atom attached to R13 and R13a, wherein the
alkylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom and may
45 optionally be substituted with a halogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R14, phenyl, phenyl substituted with (Z)q, an oxo group or a
thioxo group,
each of R14 and R14a is independently a halogen atom, cyano, nitro, C3-C8 cycloalkyl,
5
(C3-C8) cycloalkyl optionally substituted with R19, -OH, -OR15, -SH, -S(O)rR15,
-S(=NR17b)R15a, -S(O)(=NR17b)R15a, -C(O)OH, -C(O)OR15a, -C(O)SR15a, -C(S)OR15a,
-C(S)SR15a, -C(O)R16, -C(O)N(R17a)R17, -C(S)N(R17a)R17, -N(R17a)R17, -C(=NOH)R16,
-C(=NOR15)R16, -ON=C(R16a)R16, -S(O)2N(R17a)R17, -Si(R9a)(R9b)R9, -P(O)(OR10)2,
-P(S)(OR10)2, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl substituted 5 d with
(Z)q or D1-1 to D1-99,
each of R15 and R15a is independently cyano, C1-C6 alkyl, (C1-C6) alkyl optionally
substituted with R19, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R19, C2-C6
alkynyl, (C2-C6) alkynyl optionally substituted with R19, C3-C8 cycloalkyl, (C3-C8)
10 cycloalkyl optionally substituted with R19, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R19, -S(O)rR20, -C(O)OR20a, -C(O)R21, -C(O)N(R22a)R22,
-C(S)N(R22a)R22, phenyl, phenyl substituted with (Z)q2, naphthyl, naphthyl substituted
with (Z)q or D1-1 to D1-99,
each of R16 and R16a is independently a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl
15 optionally substituted with R19, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
R19, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R19, C3-C8 cycloalkyl, (C3-
C8) cycloalkyl optionally substituted with R19, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R19, -C(O)R21, phenyl, phenyl substituted with (Z)q, naphthyl,
naphthyl substituted with (Z)q or D1-1 to D1-99,
20 each of R17 and R17a is independently a hydrogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R19, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
R19, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R19, C3-C8 cycloalkyl, (C3-
C8) cycloalkyl optionally substituted with R19, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R19, -CHO, -S(O)rR20, -C(O)R21, -C(O)OR20a, -C(O)N(R22a)R22,
25 -C(S)N(R22a)R22 or -S(O)2N(R22a)R22, or R17 and R17a may form, together with each other,
a C2-C7 alkylene chain to form a 3 to 8-membered ring together with the nitrogen atom
attached to R17 and R17a, wherein the alkylene chain may contain an oxygen atom, a
sulfur atom or a nitrogen atom and may optionally be substituted with a halogen atom,
cyano, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, phenyl, phenyl
30 substituted with (Z)q, an oxo group or a thioxo group,
R17b is a hydrogen atom, cyano, nitro, -OR20, -S(O)rR20, -C(O)OR20a, -C(O)R21,
-C(O)N(R22a)R22, -C(S)N(R22a)R22 or -S(O)2N(R22a)R22,
R19 is a halogen atom, cyano, C3-C8 cycloalkyl, -OR20, -S(O)rR20, -C(O)OR20a,
-C(O)N(R22a)R22, -C(S)N(R22a)R22, -C(=NOR20)R21, -Si(R9a)(R9b)R9, phenyl, phenyl
35 substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to D1-99,
each of R20 and R21 is independently a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R32, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
R32, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R32, C3-C8 cycloalkyl, (C3-
C8) cycloalkyl optionally substituted with R32, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
40 optionally substituted with R32, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl
substituted with (Z)q or D1-1 to D1-99,
each of R20a, R22 and R22a is independently a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R32, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
R32, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R32, C3-C8 cycloalkyl, (C3-
45 C8) cycloalkyl optionally substituted with R32, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R32, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl
substituted with (Z)q or D1-1 to D1-99,
D1-1 to D1-99 are rings represented by the following structures, respectively,
6
D1-1 D1-3 D1-4
D1-18 D1-19
D1-24 D1-25
D1-26 D1-27
D1-28 D1-29 D1-30
N
N
N
N
S
N
N
O
N
N N
N
N
N
N N
N
N N
N
N
N
N
N
N
N
N
N
N N
N
N
O
(X1)g4 X1a
(X1)g2 X1a
(X1)g3
(X1)g1
D1-2
S
(X1)g1 (X1)g1
D1-5
O
N
(X1)g2
D1-6
S
N
(X1)g2
D1-7
N
N
(X1)g1
D1-8
N N
X1a
(X1)g2
D1-9
N
O
(X1)g2
D1-10
N
S
(X1)g2
D1-11
N N
(X1)g1
D1-12
N
N
X1a
(X1)g2
D1-13
N
S
N
(X1)g3
D1-14
N
N
O
(X1)g3
D1-15
N
N
S
(X1)g3
D1-16
O
N
N
D1-17
S
N
N
(X1)g3 (X1)g3 (X1)g3 (X1)g3
D1-20
N N
N
(X1)g2
D1-21
N
N
N
X1a
(X1)g3
D1-22
N
N
N
(X1)g2
D1-23
N
N N
X1a
(X1)g3
(X1)g2
(X1)g3
X1a
(X1)g3 X1a
(X1)g3
7
D1-33
N
(X1)g4
D1-42
N
N
N
N (X1)g3
N
N N
N
D1-31
X1a
(O)m3
D1-35
N
N
(X1)g1
D1-36
N
N
(X1)g1
D1-39
N
N
(X1)g1
D1-40
N
N
N
(X1)g2
D1-41
N
N
N
(X1)g2
D1-34
N
(X1)g4
D1-32
N
(O)m3 (X1)g4 (O)m3
D1-37
N
N
(X1)g1
D1-38
N
N
(X1)g1
N
N
(X1b)f6 (X1)g3
(X1b)f5
D1-43 D1-44
O
N
(X1b)f4
D1-45
O
N N N
X1a
(X1b)f4
(X1)g3
(X1b)f1
D1-46 D1-47
N
N O
N
O
N
(X1)g3
(X1b)f1
(X1b)f1
(X1b)f4
R12
(X1)g3
D1-48 D1-49 D1-50
S
N
S
N
(X1)g3
(X1b)f1
(X1b)f4
D1-51 D1-52
N
O
(X1b)f6
N
N N
N
(X1)g3
(X1b)f1
(X1b)f4
X1a X1a
D1-53 D1-54 D1-55
O
N N
N
(X1b)f6
X1a (X1)g3
(X1b)f5
D1-56 D1-57
O
N
(X1b)f6
O N
(X1b)f5
(X1)g3
N
N
(X1)g3
(X1b)f5
X1a
D1-58 D1-59 D1-60
S
N
(X1b)f6 N
N
(X1b)f6
N N
(X1b)f5
(X1)g3
X1a
X1a
S N
(X1b)f5
(X1)g3
O
O
N
(X1b)f2
D1-61 D1-62 D1-63 D1-64 D1-65
8
X1 is a halogen atom, cyano, nitro, -OH, -SH or R24, provided that when g1, g2 or g4 is
an integer of at least 2, each X1 may be identical with or different from one another, and
when there are two neighboring X1’s, the two neighboring X1’s may form -CH2CH2CH2-,
-CH2CH2O-, -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -CH2CH2CH2CH2-,
-CH2CH2CH2O-, -CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH2O-, -CH2CH2CH2S- 5 or
-OCH2CH2S- to form, together with the carbon atoms attached to the X1’s, a 5-
membered ring or 6-membered ring which may have one or more hydrogen atoms on
O
N
O O
O N
(X1b)f4
(X1b)f1
(X1)g3
O
S
N
O
N
N
X1a
(X1b)f2 (X1b)f2
N
N
O
(X1b)f4
X1a
O
N
(X1b)f8
D1-66 D1-67 D1-68 D1-69
D1-72
D1-76 D1-78 D1-79
O (X1b)f1
O
(X1b)f5
D1-80
S
(X1b)f5
D1-82
S
(X1b)f 7
(O)r
D1-81
O
(X1b)f7
D1-83
N
(X1b)f7
X1a
D1-84
O
O
(X1b)f5
D1-85
S
O
(X1b)f5
D1-86
N
O
(X1b)f5
X1a
D1-87
S
S
(X1b)f5
D1-88
N
S
(X1b)f 5
X1a
N
O
(X1b)f6
N
S
(X1b)f6
D1-89 D1-90
S
N
O
(X1b)f4
D1-70
O
S N
(X1b)f1
(X1)g3
D1-71
O
N N
(X1b)f1
(X1)g3
D1-73
X1a
O
N
N
N
(X1b)f4 O N
(X1b)f1
(X1)g3
D1-74 D1-75
X1a
O
N
(X1b)f8
D1-77
X1a
D1-92
O
(X1b)f9
D1-93
S
(X1b)f 9
(O)r
D1-94
N
(X1b)f9
X1a
D1-95
O
O
(X1b)f7
D1-96
S
O
(X1b)f7
D1-97
O N
(X1b)f7
X1a
D1-98
S
S
(X1b)f7
D1-99
S N
(X1b)f7
X1a
N
N
(X1b)f6
X1a
D1-91
9
the ring-constituting carbon atoms optionally replaced by one or more halogen atoms,
one or more C1-C6 alkyl groups, one or more C1-C6 haloalkyl groups, one or more C1-C6
alkoxy groups, one or more C1-C6 alkylthio groups, one or more C1-C6 alkylsulfinyl
groups or one or more C1-C6 alkylsulfonyl groups,
X1a is a hydrogen atom, cyano, -OH or 5 R24,
X1b is a halogen atom, cyano, nitro, -OH, -SH or R24, provided that when f1, f2, f4, f5, f6,
f7, f8 or f9 is an integer of at least 2, each X1b may be identical with or different from one
another, and when there are two X1b’s on the same carbon, the two X1b’s may form oxo,
thioxo, imino, C1-C6 alkylimino, C1-C6 alkoxyimino or C1-C6 alkylidene together with
10 each other,
Z is a halogen atom, cyano, nitro, -OH, -SH or R24, provided that q is an integer of at
least 2, each Z may be identical with or different from one another, and when there are
two neighboring Z’s, the two neighboring Z’s may form -CH2CH2CH2-, -CH2CH2O-,
-CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -CH2CH2CH2CH2-, -CH2CH2CH2O-,
15 -CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH2O-, -CH2CH2CH2S- or -OCH2CH2S- to form,
together with the carbon atoms attached to the Z’s, a 5-membered ring or a 6-
membered ring which may have one or more hydrogen atoms on the ring-constituting
carbon atoms optionally replaced by one or more halogen atoms, one or more C1-C6
alkyl groups, one or more C1-C6 haloalkyl groups, one or more C1-C6 alkoxy groups, one
20 or more C1-C6 alkylthio groups, one or more C1-C6 alkylsulfinyl groups or one or more
C1-C6 alkylsulfonyl groups,
Z3 is a halogen atom, nitro, -OH, -SH or R24, provided that q is an integer of at least 2,
each Z3 may be identical with or different from one another, and when there are two
neighboring Z3’s, the neighboring two Z’s may form -CH2CH2CH2-, -CH2CH2O-,
25 -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -CH2CH2CH2CH2-, -CH2CH2CH2O-,
-CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH2O-, -CH2CH2CH2S- or -OCH2CH2S- to form,
together with the carbon atoms attached to the Z3’s, a 5-membered ring or a 6-
membered ring which may have one or more hydrogen atoms on the ring-constituting
carbon atoms optionally replaced by one or more halogen atoms, one or more C1-C6
30 alkyl groups, one or more C1-C6 haloalkyl groups, one or more C1-C6 alkoxy groups, one
or more C1-C6 alkylthio groups, one or more C1-C6 alkylsulfinyl groups or one or more
C1-C6 alkylsulfonyl groups,
R24 is a C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28, C2-C6 alkenyl, (C2-C6)
alkenyl optionally substituted with R28, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
35 optionally substituted with R28, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with
R28, C3-C8 cycloalkyl, (C3-C8) cycloalkyl optionally substituted with R28, -OR25, -S(O)rR25,
-C(O)OH, -C(O)OR25a, -C(O)R26, -C(O)N(R27a)R27, -C(S)N(R27a)R27, -N(R27a)R27, -
C(=NOR25)R26 or -S(O)2N(R27a)R27,
each of R25, R25a and R26 is independently C1-C6 alkyl or (C1-C6) alkyl optionally
40 substituted with R32a,
each of R27 and R27a is independently a hydrogen atom, C1-C6 alkyl, -S(O)rR34 or
-C(O)R34,
each of R28 and R28a is independently a halogen atom, -OH, -OR29, -SH or -S(O)rR29,
each of R29 and R33 is independently C1-C6 alkyl,
45 each of R32 and R32a is independently a halogen atom, -OR33 or -S(O)rR33,
R34 is C1-C6 alkyl, C3-C8 cycloalkyl or C1-C6 haloalkyl,
each of n, g1 and f1 is independently an integer of from 0 to 3,
each of g2 and f2 is independently an integer of from 0 to 2,
10
g3 is an integer of from 0 to 1,
each of g4 and f4 is independently an integer of from 0 to 4,
f5 is an integer of from 0 to 5,
f6 is an integer of from 0 to 6,
f7 is an integer of from 0 to 75 ,
f8 is an integer of from 0 to 8,
f9 is an integer of from 0 to 9,
q is independently an integer of from1 to 5,
q2 is an integer of from 0, 1 or 3 to 5,
10 each of m1, m2 and m3 is independently an integer of from 0 or 1, and
r is an integer of from 0 to 2.
[2] The pyrazole derivative or a salt thereof according to [1], wherein Rb is -C(O)R7,
-C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(S)OR6a, -C(S)SR6a, -C(O)N(R8a)R8, -C(S)N(R8a)R8,
-C(O)N(R8b)N(R8a)R8, -C(O)N(R8a)OR6a, -C(=NR8b)OR6a, -C(=NR8b)SR6a,
15 -C(=NR8b)N(R8a)R8, -C(=NR8b)R7, D1-49, D1-51, D1-53, D1-59, D1-61 or D1-63, or Rb
may form =C(Rb2)Rb3 together with Ra.
[3] The pyrazole derivative or a salt thereof according to [2], wherein A1 is -CR1,
each of R1 and R3 is independently a hydrogen atom, a halogen atom, cyano, -NH2, C1-
C6 alkyl, (C1-C6) alkyl optionally substituted with R28a, C1-C6 alkoxy, C1-C6 alkylthio, C1-
20 C6 alkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 alkoxycarbonyl,
R2 is a halogen atom, C1-C6 alkyl or C1-C6 alkoxy, and
R4 is a hydrogen atom, a halogen atom, cyano, -NH2, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R28a, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6
alkylsulfonyl.
25 [4] The pyrazole derivative or a salt thereof according to [2], wherein A1 is -N(-O)m2,
R2 is a halogen atom, C1-C6 alkyl or C1-C6 alkoxy, and
each of R3 and R4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-
C6 alkoxy.
[5] The pyrazole derivative or a salt thereof according to [3], wherein R1 is a hydrogen
30 atom, a halogen atom, cyano, -NH2, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy,
R2 is C1-C6 alkyl,
R3 is a hydrogen atom, a halogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl optionally
substituted with R28a, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl or C1-C6
alkoxycarbonyl,
35 R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 alkylthio,
Ra is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R5, C2-C6
alkenyl, C2-C6 alkynyl, -S(O)rR6, -C(O)R7a, -C(O)OR6a, -NR8cR8d or -C(=NR8b)R7a,
Rb is -C(O)R7, -C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(O)N(R8a)R8, -C(S)N(R8a)R8,
-C(O)N(R8b)N(R8a)R8, -C(=NR8b)SR6a, -C(=NR8b)N(R8a)R8, -C(=NR8b)R7 or D1-51, or Rb
40 may form =C(Rb2)Rb3 together with Ra,
Rb2 is a hydrogen atom, C1-C6 alkyl or -S(O)rR6,
Rb3 is (C1-C6) alkyl optionally substituted with R14, -OR6 or -N(R8b)R8, or Rb3 may form,
together with Rb2, a C4 alkylene chain to form a 5-membered ring together with the
carbon atom attached to Rb3 and Rb2, wherein the alkylene chain may contain a sulfur
45 atom and a nitrogen atom and may optionally be substituted with -C(O)R7,
R5 is a halogen atom, cyano, C3-C8 cycloalkyl, -OR11, -S(O)rR11, -C(O)OR11a,
-C(=NOR11)R12, -Si(R9a)(R9b)R9, phenyl or D1-37,
R6 is C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R14,
11
R6a is C1-C6 alkyl or phenyl substituted with (Z)q,
R7 is C1-C15 alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8 cycloalkyl, (C3-C8)
cycloalkyl optionally substituted with R14, C2-C6 alkenyl, (C2-C6) alkenyl optionally
substituted with R14, C3-C8 cycloalkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally
substituted with R14, -C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13, -C(=NOR11)R12, 5 , phenyl
substituted with (Z)q, D1-1, D1-2, D1-4, D1-5, D1-6, D1-8, D1-9, D1-10, D1-12, D1-13,
D1-19, D1-32, D1-33, D1-35, D1-38, D1-45, D1-81, D1-82, D1-87, D1-88, D1-92 or D1-
94, or R7 may form, together with Ra, a C2-C4 alkylene chain or a C2-C4 alkenylene
chain containing a double bond to form a 4 to 6-membered ring together with the carbon
10 atom attached to R7 and the nitrogen atom attached to Ra, wherein the alkylene chain
may contain one or two oxygen atoms or nitrogen atoms and may optionally be
substituted with a halogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14,
-OR11, -S(O)rR11, an oxo group or a methylidene group,
R7a is a hydrogen atom or C1-C6 alkyl,
15 R8 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8
cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, -C(O)R12, -C(O)OR11a, -C(=NOR11)R12,
-S(O)2R11a, phenyl, phenyl substituted with (Z)q, D1-32, D1-33, D1-34 or D1-80,
R8a is a hydrogen atom, C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R14a, or
R8a may form, together with Ra, a C2-C3 alkylene chain to form a 5 to 6-membered ring
20 together with the nitrogen atom attached to R8a and the nitrogen atom attached to Ra,
wherein the alkylene chain may contain an oxygen atom and may optionally be
substituted with (C1-C6) alkyl optionally substituted with R14 or an oxo group, or R8 and
R8a may form, together with each other, a C5 alkylene chain to form a 6-membered ring
together with the nitrogen atom attached to R8 and R8a, wherein the alkylene chain may
25 optionally be substituted with C1-C6 alkyl, or R8 may form =C(R8f)R8e together with R8a,
R8b is a hydrogen atom, cyano, C1-C6 alkyl or -OR11,
R8c is a hydrogen atom, C1-C6 alkyl or -C(O)OR11a,
R8d is a hydrogen atom, -C(O)OR11a or -C(O)R12,
R8e is a hydrogen atom,
30 R8f is -N(R13a)R13,
each of R9, R9a, R9b and R10 is independently C1-C6 alkyl,
R11 is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14a or C1-C6 alkenyl,
R11a is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14a or phenyl,
R12 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14a, C3-C8
35 cycloalkyl, -C(=NOR15)R16 or D1-2,
R13 is C1-C6 alkyl or phenyl,
R13a is a hydrogen atom or C1-C6 alkyl,
R14 is a halogen atom, cyano, C3-C8 cycloalkyl, -OH, -OR15, -SH, -S(O)rR15,
-S(=NR17b)R15a, -S(O)(=NR17b)R15a, -C(O)OH, -C(O)OR15a, -C(O)N(R17a)R17,
40 -C(=NOR15)R16, -N(R17a)R17, -ON=C(R16a)R16, -S(O)2N(R17a)R17, -Si(R9a)(R9b)R9,
-P(O)(OR10)2, phenyl, phenyl substituted with (Z)q, D1-1, D1-2, D1-5, D1-7, D1-8, D1-28,
D1-32, D1-33, D1-34, D1-84, D1-85, D1-87, D1-93 or D1-98,
R14a is a halogen atom, -OR15, -S(O)rR15, -Si(R9a)(R9b)R9 or phenyl,
R15 is cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C1-C6) alkyl optionally
45 substituted with R19, -C(O)R21, phenyl substituted with (Z)q2, D1-12, D1-32, D1-37 or
D1-51,
R15a is C1-C6 alkyl,
R16 is C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R19,
12
R16a is a hydrogen atom,
R17 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R19,
-S(O)rR20, -C(O)OR20a, -C(O)R21, -C(O)N(R22a)R22, -C(S)N(R22a)R22, -C(=NOR20)R21,
-S(O)2N(R22a)R22 or phenyl,
R17a is a hydrogen atom or C1-C6 alkyl, or R17a may form =C(R17c)R17d together with 5 th R17,
R17b is cyano,
R17c is -N(R22a)R22,
R17d is a hydrogen atom,
R19 is a halogen atom, cyano, C3-C8 cycloalkyl, -OR20, -S(O)rR20, -C(O)OR20a,
10 -C(O)N(R22a)R22, -C(=NOR20)R21, -Si(R9a)(R9b)R9, phenyl or D1-34,
R20 is C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R32,
R20a is C1-C6 alkyl,
R21 is a hydrogen atom, C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R32,
R22 is C1-C6 alkyl,
15 R22a is a hydrogen atom or C1-C6 alkyl,
X1 is a halogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with
R28, C3-C8 cycloalkyl, -OR25, -S(O)rR25, -C(O)R26, -C(=NOR25)R26 or -S(O)2N(R27a)R27,
provided that when g2 is an integer of 2, each X1 may be identical with or different from
each other,
20 X1a is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28, -C(O)OR25a or -C(O)R26,
X1b is (C1-C6) alkyl optionally substituted with R28, provided that when f5 is an integer of
3, each X1b may be identical with or different from one another, and when there are two
X1b’s on the same carbon, the two X1b’s may form oxo together with each other,
Z is a halogen atom, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28,
25 -S(O)rR25, -C(O)OH or -C(O)N(R27a)R27, provided that when q is an integer of at least 2,
and there are two neighboring Z’s , the two neighboring Z’s may form -OCH2O- to form,
together with the carbon atoms attached to the Z’s, a 5-membered ring which may have
one or more hydrogen atoms on the ring-constituting carbon atoms optionally replaced
by one or more halogen atoms,
30 each of R25 and R26 is independently C1-C6 alkyl or (C1-C6) alkyl optionally substituted
with R32a,
each of R25a, R29, R33 and R34 is independently C1-C6 alkyl,
R27 is a hydrogen atom or -S(O)rR34,
R27a is a hydrogen atom,
35 each of R28 and R28a is independently a halogen atom, -OH, -OR29 or -S(O)rR29,
R32 is a halogen atom, -OR33 or -S(O)rR33,
R32a is a halogen atom or -S(O)rR33,
n is an integer of from 0 to 1,
each of g1 and g2 is independently an integer of from0 to 2,
40 each of g3, f7, f9 and m3 is independently an integer of 0,
g4 is an integer of from 0 to 1,
f5 is an integer of from 0 to 3,
q is an integer of from 1 to 2,
q2 is an integer of 1, and
45 r is an integer of from 0 to 2.
[6] The pyrazole derivative or a salt thereof according to [3], wherein R1, R2 and R4
are hydrogen atoms,
Ra is a hydrogen atom or C1-C6 alkyl,
13
Rb is -C(O)R7, -C(O)OR6a, -C(O)N(R8a)R8 or -C(=NR8b)N(R8a)R8,
each of R6a, R11 and R15 is independently C1-C6 alkyl,
R7 is C1-C6 alkyl, C1-C6 alkyl optionally substituted with R14, C1-C6 alkenyl optionally
substituted with R14or D1-8, or R7 may form, together with Ra, a C3-C4 alkylene chain or
a C3-C4 alkenylene chain containing a double bond to form a 5 to 6-membered ri5 ng
together with the carbon atom attached to R7 and the nitrogen atom attached to Ra,
wherein the alkylene chain may contain an oxygen atom and may optionally be
substituted with a halogen atom, (C1-C6) alkyl optionally substituted with R14or -S(O)rR11,
R8 is C1-C6 alkyl or C1-C6 alkyl optionally substituted with R14,
10 R8a is a hydrogen atom, or R8a may form, together with Ra, a C2 alkylene chain to form a
6-membered ring together with the nitrogen atom attached to R8a and the nitrogen atom
attached to Ra, wherein the alkylene chain may contain an oxygen atom,
R8b is cyano,
R14 is a halogen atom, -OH, -S(O)rR15 or phenyl substituted with (Z)q,
15 each of X1a and Z is independently C1-C6 haloalkyl,
g2 is an integer of 0,
q is an integer of 1, and
r is an integer of from 0 to 2.
[7] The pyrazole derivative or a salt thereof according to [1], wherein R1, R2 and R4
20 are hydrogen atoms,
Ra is a hydrogen atom or C1-C6 alkyl,
Rb is -S(O)rR6,
R6 is C1-C6 alkyl, C2-C6 alkenyl or (C1-C6) alkyl optionally substituted with R14,
R14 is -S(O)rR15,
25 R15 is C1-C6 alkyl, and
r is an integer of from 0 to 2.
[8] The pyrazole derivative or a salt thereof according to [5], wherein R7 is C1-C15
alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8 cycloalkyl, (C3-C8) cycloalkyl
optionally substituted with R14, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
30 R14, C3-C8 cycloalkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R14,
-C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13, -C(=NOR11)R12, phenyl substituted with (Z)q,
D1-1, D1-2, D1-4, D1-5, D1-6, D1-8, D1-9, D1-10, D1-12, D1-13, D1-19, D1-32, D1-33,
D1-35, D1-38, D1-45, D1-81, D1-82, D1-87, D1-88, D1-92 or D1-94,
R8a is a hydrogen atom, C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R14a, or
35 R8 may form, together with R8a, a C5 alkylene chain to form a 6-membered ring together
with the nitrogen atom attached to R8 and R8a, wherein the alkylene chain may
optionally be substituted with C1-C6 alkyl, or R8 and R8a may form =C(R8f)R8e together
with each other.
[9] The pyrazole derivative or a salt thereof according to [5], wherein R7 is C1-C6 alkyl,
40 (C1-C6) alkyl optionally substituted with R14, C3-C8 cycloalkyl, (C3-C8) cycloalkyl
optionally substituted with R14, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
R14, C3-C8 cycloalkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R14,
-C(O)R12, -C(=NOR11)R12, D1-1, D1-2, D1-5, D1-6, D1-8, D1-10, D1-12, D1-13, D1-19,
D1-32, D1-33, D1-35, D1-38, D1-45, D1-81, D1-82, D1-87 or D1-88, and
45 R8a is a hydrogen atom or C1-C6 alkyl.
[10] The pyrazole derivative or a salt thereof according to [5], wherein R7 is C1-C6 alkyl,
(C1-C6) alkyl optionally substituted with R14, C3-C8 cycloalkyl, (C3-C8) cycloalkyl
optionally substituted with R14, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
14
R14, C3-C8 cycloalkenyl, -C(O)R12, -C(=NOR11)R12, D1-8 or D1-82, and
R8a is a hydrogen atom or C1-C6 alkyl.
[11] The pyrazole derivative or a salt thereof according to [5], wherein R7 is C1-C6 alkyl,
(C1-C6) alkyl optionally substituted with R14, C2-C6 alkenyl, (C2-C6) alkenyl optionally
substituted with R1, -C(O)R12, -C(=NOR11)R12, D1-8 or D1-82, 5 and
R8a is a hydrogen atom or C1-C6 alkyl.
[12] The pyrazole derivative or a salt thereof according to [5], wherein R7 is C1-C6 alkyl,
C1-C6 alkyl optionally substituted with R14, C1-C6 alkenyl optionally substituted with R14,
-C(O)R12, D1-8 or D1-82, and
10 R8a is a hydrogen atom or C1-C6 alkyl.
[13] The pyrazole derivative or a salt thereof according to [5], wherein R7 may form,
together with Ra, a C2-C4 alkylene chain or a C2-C4 alkenylene chain containing a
double bond to form a 4 to 6-membered ring together with the carbon atom attached to
R7and the nitrogen atom attached to Ra, wherein the alkylene chain may contain one or
15 two oxygen atoms or nitrogen atoms and may optionally be substituted with a halogen
atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, -OR11, -S(O)rR11, an oxo
group or a methylidene group,
R8 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8
cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, -C(O)R12, -C(O)OR11a, -C(=NOR11)R12,
20 -S(O)2R11a, phenyl, phenyl substituted with (Z)q, D1-32, D1-33, D1-34 or D1-80,
R8a may form, together with Ra, a C2-C3 alkylene chain to form a 5 to 6-membered ring
together with the nitrogen atom attached to R8aand the nitrogen atom attached to Ra,
wherein the alkylene chain may contain an oxygen atom and may optionally be
substituted with (C1-C6) alkyl optionally substituted with R14or an oxo group,
25 R14 is a halogen atom or -S(O)rR15, and
R15 is C1-C6 alkyl.
[14] The pyrazole derivative or a salt thereof according to [5], wherein R7 may form,
together with Ra, a C2-C4 alkylene chain or a C2-C4 alkenylene chain containing a
double bond to form a 4 to 6-membered ring together with the carbon atom attached to
30 R7and the nitrogen atom attached to Ra, wherein the alkylene chain may contain one or
two oxygen atoms or nitrogen atoms and may optionally be substituted with a halogen
atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, -OR11, -S(O)rR11, an oxo
group or a methylidene group,
R8 is a hydrogen atom or C1-C6 alkyl optionally substituted with R14,
35 R8a may form, together with Ra, a C2 alkylene chain to form a 5 to 6-membered ring
together with the nitrogen atom attached to R8a and the nitrogen atom attached to Ra,
wherein the alkylene chain may contain an oxygen atom and may optionally be
substituted with (C1-C6) alkyl optionally substituted with R14or an oxo group,
R14 is a halogen atom or -S(O)rR15, and
40 R15 is C1-C6 alkyl.
[15] The pyrazole derivative or a salt thereof according to [5], wherein R7 may form,
together with Ra, a C3-C4alkylene chain or a C3-C4 alkenylene chain containing a double
bond to form a 5 to 6-membered ring together with the carbon atom attached to R7 and
the nitrogen atom attached to Ra, wherein the alkylene chain may contain an oxygen
45 atom and may optionally be substituted with a halogen atom, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R14, -S(O)rR11, oxo group or a methylidene group,
R8 is a hydrogen atom or C1-C6 alkyl optionally substituted with R14,
R8a may form, together with Ra, a C2 alkylene chain to form a 5- to 6-membered ring
15
together with the nitrogen atom attached to R8a and the nitrogen atom attached to Ra,
wherein the alkylene chain may contain an oxygen atom and may optionally be
substituted with (C1-C6) alkyl optionally substituted with R14or an oxo group,
R14 is a halogen atom or -S(O)rR15, and
R15 is C1-C6 alkyl5 .
[16] The pyrazole derivative or a salt thereof according to [5], wherein R7 may form,
together with Ra, a C3-C4 alkylene chain or a C3-C4 alkenylene containing a double bond
to form a 5- to 6-membered ring together with the carbon atom attached to R7 and the
nitrogen atom attached to Ra, wherein the alkylene chain may contain an oxygen atom
10 and may optionally be substituted with a halogen atom, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R14, -S(O)rR11, oxo group or a methyliedene group,
R8 is C1-C6 alkyl optionally substituted with R14,
R8a may form, together with Ra, a C2 alkylene chain to form a 6-membered ring together
with the nitrogen atom attached to R8a and the nitrogen atom attached to Ra, wherein
15 the alkylene chain may contain an oxygen atom, and
R14 is a halogen atom.
[17] The pyrazole derivative or a salt thereof according to [4] wherein R4 is a hydrogen
atom,
R3 is a halogen atom,
20 Ra is C1-C6 alkyl,
Rb is -C(O)R7,
R7 is (C1-C6) alkyl optionally substituted with R14,
R14 is -S(O)rR15,
R15 is C1-C6 alkyl, and
25 m2, n and r are integers of 0.
[18] A pesticide containing one or more pyrazole derivatives or salts thereof selected
from the pyrazole derivatives and salts thereof as defined in [1] to [17], as active
ingredient(s).
[19] An agrochemical containing one or more pyrazole derivatives or salts thereof
30 selected from the pyrazole derivatives and salts thereof as defined in [1] to [17], as
active ingredient(s).
[20] A parasticide for an internal or external parasite in or on a mammal or bird, which
contains one or more pyrazole derivatives or salts thereof selected from the pyrazole
derivatives and salts thereof as defined in [1] to [17], as active ingredient(s).
35 [21] An insecticide or miticide containing one or more pyrazole derivatives or salts
thereof selected from the pyrazole derivatives and salts thereof as defined in [1] to [17],
as active ingredient(s).
[22] A seed treatment agent containing one or more pyrazole derivatives or salts
thereof selected from the pyrazole derivatives and salts thereof as defined in [1] to [17],
40 as active ingredient(s).
[23] The seed treatment agent according to [22], which is used to treat seeds by
dipping.
[24] A soil treatment agent containing one or more pyrazole derivatives or salts thereof
selected from the pyrazole derivatives and salts thereof as defined in [1] to [17], as
45 active ingredient(s).
[25] The soil treatment agent according to [24], which is used to treat soil by irrigation.
ADVANTAGEOUS EFFECT(S) OF INVENTION
16
The compounds of the present invention have excellent insecticidal and miticidal
activities on many agricultural pest insects, spider mites, internal or external mammal or
bird parasites and have sufficient controlling effect on pest insects which have acquired
resistance to conventional insecticides. The compounds of the present invention have
little harmful effect on mammals, fish and beneficial insects, show low persistence 5 stence and
are environmentally friendly.
Thus, the present invention can provide useful novel pesticides.
DESCRIPTION OF EMBODIMENT(S)
10 The compounds of the present invention can have geometrical isomers such as Eisomers
and Z-isomers, depending on the types of substituents in them, and the present
invention covers both E-isomers and Z-isomers and mixtures containing them in any
ratios. The compounds of the present invention can have optically active isomers due
to the presence of one or more asymmetric carbon atoms, and the present invention
15 covers any optically active isomers and any racemates.
Some of the compounds of the present invention can be converted, by ordinary
methods, to acid addition salts with hydrogen halides such as hydrofluoric acid,
hydrochloric acid, hydrobromic acid and hydroiodic acid, with inorganic acids such as
nitric acid, sulfuric acid, phosphoric acid, chloric acid and perchloric acid, with sulfonic
20 acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesuflonic acid,
benzenesulfonic acid and p-toluenesulfonic acid, with carboxylic acids such as formic
acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic
acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid,
lactic acid, gluconic acid and citric acid, with amino acids such as glutamic acid aspartic
25 acid.
Some of the compounds of the present invention can be converted, by ordinary
methods, to metal salts with alkali metals such as lithium sodium and potassium, with
alkaline earth metals such as calcium, barium and magnesium, with metals such as
aluminum.
30 Next, specific examples of each substituent used herein will be given below. ndenotes
normal, i- iso, s- secondary, tert- tertiary, and Ph phenyl.
As a halogen atom in the compounds of the present invention, a fluorine atom, a
chlorine atom, a bromine atom or an iodine atom may be mentioned. Herein, the
expression “halo” also means such a halogen atom.
35 The expression Ca-Cb alkyl herein means a linear or branched hydrocarbon group
containing from a to b carbon atoms such as a methyl group, an ethyl group, a n-propyl
group, an i-propyl group, a n-butyl group, an i-butyl group, a s-butyl group, a t-butyl
group, a n-pentyl group, a 1,1-dimethylpropyl group or a n-hexyl group, and those within
the designated carbon number range are selected.
40 The expression Ca-Cb haloalkyl herein means a linear or branched hydrocarbon
group containing from a to b carbon atoms in which hydrogen atom(s) on carbon
atom(s) are optionally substituted with halogen atom(s) which may be identical with or
different from one another if two or more halogen atoms are present, such as a
fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a
45 difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a
chlorodifluoromethyl group, a trichloromethyl group, a bromodifluoromethyl group, a 2-
fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluoroethyl group,
a 2,2,2-trifluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2,2,2-trichloroethyl
17
group, a 1,1,2,2-tetrafluoroethyl group, a 2-chloro-1,1,2-trifluoroethyl group, a
pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group,
a 1,1,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 2,2,2-trifluoro-1-
(trifluoromethyl)ethyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl group,a
2,2,3,3,4,4,4-heptafluorobutyl group or a nonafluorobutyl group, and those within 5 the
designated carbon number range are selected.
The expression Ca-Cb cycloalkyl herein means a cyclic hydrocarbon group
containing from a to b carbon atoms in the form of a 3- to 6-membered monocyclic or
polycyclic ring which may optionally be substituted with an alkyl group as long as the
10 number of carbon atoms does not exceed the designated carbon number range, such
as a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a
2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl
group, and those within the designated carbon number range are selected.
The expression Ca-Cb halocycloalkyl means a cyclic hydrocarbon group containing
15 from a to b carbon atoms in the form of a 3- to 6-membered monocyclic or polycyclic
ring which may optionally be substituted with an alkyl group as long as the number of
carbon atoms does not exceed the designated carbon number range, in which hydrogen
atom(s) on carbon atom(s) in a ring moiety and/or in a side chain are optionally
substituted with halogen atom(s) which may be identical with or different from one
20 another if two or more halogen atoms are present, such as a 2,2-difluorocyclopropyl
group, a 2,2-dichlorocyclopropyl group, a 2,2-dibromocyclopropyl group, a 2,2-difluoro1-
methylcyclopropyl group, a 2,2-dichloro-1-methylcyclopropyl group, a 2,2-dibromo-1-
methylcyclopropyl group or a 2,2,3,3-tetrafluorocyclobutyl group, and those within the
designated carbon atom range are selected.
25 The expression Ca-Cb alkenyl herein means a linear or branched unsaturated
hydrocarbon group containing from a to b carbon atoms and having one or more double
bonds in the molecule such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a
1-methylethenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 3-methyl-2-
butenyl group or a 1,1-dimethyl-2-propenyl group, and those within the designated
30 carbon atom range are selected.
The expression Ca-Cb haloalkenyl herein means a linear or branched unsaturated
hydrocarbon group containing from a to b carbon atoms and having one or more double
bonds in the molecule, in which hydrogen atom(s) on carbon atom(s) are optionally
substituted with halogen atom(s) which may be identical with or different from one
35 another if two or more halogen atoms are present, such as a 2,2-dichlorovinyl group, a
2-fluoro2-propenyl group, a 2-chloro-2-propenyl group, a 3-chloro-2-propenyl group, a
2-bromo-2-propenyl group, a 3,3-difluoro-2-propenyl group, a 2,3-dichloro-2-propenyl
group, a 3,3-dichloro-2-propenyl group, a 2,3,3-trifluoro-2-propenyl group, a 2,3,3-
trichloro-2-propenyl group, a 1-(trifluoromethyl)ethenyl group, a 4,4-difluoro-3-butenyl
40 group, a 3,4,4-trifluoro-3-butenyl group or a 3-chloro-4,4,4-trifluoro-2-butenyl group, and
those within the designated carbon atom range are selected.
The expression Ca-Cb cycloalkenyl herein means a cyclic unsaturated
hydrocarbon group containing from a to b carbon atoms and containing one or more
end or exo double bonds in the form of a 3- to 6-membered monocyclic or polycyclic
45 ring which may optionally be substituted with an alkyl group as long as the number of
carbon atoms does not exceed the designated carbon number range, such as a 1-
cyclopenten-1-yl group, a 2-cyclopenten-1-yl group, a 1-cyclohexen-1-yl group or a 2-
cyclohexen-1-yl group, and those within the designated carbon atom range are selected.
18
The expression Ca-Cb alkylidene herein means a linear or branched hydrocarbon
group containing from a to b carbon atoms which attaches by a double bond , such as a
methylidene group, an ethylidene group, a propylidene group or a 1-methylethylidene
group, and those within the designated carbon number range are selected.
The expression Ca-Cb alkynyl herein means a linear or branched unsaturat5 ed
hydrocarbon group containing from a to b carbon atoms and having one or more triple
bonds in the molecule such as an ethynyl group, a 1-propynyl group, a 2-propynyl group,
a 1-butynyl group, a 2-butylnyl group, a 3-butynyl group or a 1,1-dimethyl-2-propynyl
group, and those within the designated carbon atom range are selected.
10 The expression Ca-Cb haloalkynyl herein means a linear or branched unsaturated
hydrocarbon group containing from a to b carbon atoms and having one or more triple
bonds in the molecule, in which hydrogen atom(s) on carbon atom(s) are optionally
substituted with halogen atom(s) which may be identical with or different from one
another if two or more halogen atoms are present, such as a 2-chloroethynyl group, a 2-
15 bromoethynyl group, a 2-iodoethynyl group, a 3-chloro-2-propynyl group or a 3-bromo-
2-propynyl group, a 3-iodo-2-propynyl group, and those within the designated carbon
number range are selected.
The expression Ca-Cb alkoxy herein means an alkyl-O- group in which the alkyl is
a previously mentioned alkyl group containing from a to b carbon atoms, such as a
20 methoxy group, an ethoxy group, a n-propyloxy group, an i-propyloxy group, a nbutyloxy
group, an i-butyloxy group, a s-butyloxy group or a tert-butyloxy group, and
those within the designated carbon atom range are selected.
The expression Ca-Cb haloalkoxy herein means a haloalkyl-O- group in which the
haloalkyl is a previously mentioned haloalkyl group containing from a to b carbon atoms,
25 such as a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy
group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group,
a 2,2,2-trifluoroethoxy group, a 1,1,2,2,-tetrafluoroethoxy group, a 2-chloro-1,1,2-
trifluoroethoxy group or a 1,1,2,3,3,3-hexafluoropropyloxy group, and those within the
designated carbon atom range are selected.
30 The expression Ca-Cb alkylthio herein means an alkyl-S- group in which the alkyl
is a previously mentioned alkyl group containing from a to b carbon atoms, such as a
methylthio group, an ethylthio group, a n-propylthio group, an i-propylthio group, a nbutylthio
group, an i-butylthio group, a s-butylthio group or a tert-butylthio group, and
those within the designated carbon atom range are selected.
35 The expression Ca-Cb haloalkylthio herein means a haloalkyl-S- group in which
the haloalkyl is a previously mentioned haloalkyl group containing from a to b carbon
atoms, such as a difluoromethylthio group, a trifluoromethylthio group, a
chlorodifluoromethylthio group, a bromodifluoromethylthio group, a 2,2,2-
trifluoroethylthio group, a 1,1,2,2-tetrafluoroethylthio group, a 2-chloro-1,1,2-
40 trifluoroethylthio group, a pentafluoroethylthio group, a 1,1,2,3,3,3-hexafluoropropylthio
group, a heptafluoropropylthio group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio
group or a nonafluorobutylthio group, and those within the designated carbon atom
range are selected.
The expression Ca-Cb alkylsulfinyl herein means an alkyl-S(O)- group in which the
45 alkyl is a previously mentioned alkyl group containing from a to b carbon atoms, such as
a methylsulfinyl group, an ethylsulfinyl group, a n-propylsulfinyl group, an i-propylsulfinyl
group, a n-butylsulfinyl group, an i-butylsulfinyl group, a s-butylsulfinyl group or a tertbutylsulfinyl
group , and those within the designated carbon atom range are selected.
19
The expression Ca-Cb haloalkylsulfinyl herein means a haloalkyl-S(O)- group in
which the haloalkyl is a previously mentioned haloalkyl group containing from a to b
carbon atoms, such as a difluoromethylsulfinyl group, a trifluoromethylsulfinyl group, a
chlorodifluoromethylsulfinyl group, a bromodifluoromethylsulfinyl group, a 2,2,2-
trifluoroethylsulfinyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl group 5 oup or a
nonafluorobutylsulfinyl group , and those within the designated carbon atom range are
selected.
The expression Cα-Cb alkylsulfonyl herein means an alkyl-SO2- group in which the
alkyl is a previously mentioned alkyl group containing from a to b carbon atoms, such as
10 a methylsulfonyl group, an ethylsulfonyl group, a n-propylsulfonyl group, an ipropylsulfonyl
group, a n-butylsulfonyl group, an i-butylsulfonyl group, a s-butylsulfonyl
group or a tert-butylsulfonyl group, and those within the designated carbon atom range
are selected.
The expression Ca-Cb haloalkylsulfonyl herein means a haloalkyl-SO2- group in
15 which the haloalkyl is a previously mentioned haloalkyl group containing from a to b
carbon atoms, such as a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a
chlorodifluoromethylsulfonyl group, a bromodifluoromethylsulfonyl group, a 2,2,2-
trifluoroethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonyl group or a 2-chloro-1,1,2-
trifluoroethylsulfonyl group, and those within the designated carbon atom range are
20 selected.
The expression Ca-Cb alkylamino herein means an amino group in which either
hydrogen atom is replaced by a previously mentioned alkyl group containing from a to b
carbon atoms, such as a methylamino group, an ethylamino group, a n-propylamino
group, an i-propylamino group, a n-butylamino group, an i-butylamino group or a tert25
butylamino group, and those within the designated carbon atom range are selected.
The expression di(Ca-Cb alkyl)amino herein means an amino group in which both
hydrogen atoms are replaced by previously mentioned alkyl groups containing from a to
b carbon atoms which may be identical with or different from each other, such as a
dimethylamino group, an ethyl(methyl)amino group, a diethylamino group, a n30
propyl(methyl)amino group, an i-propyl(methyl)amino group, a di(n-propyl)amino group
or a di(n-butyl)amino group, and those within the designated carbon atom range are
selected.
The expression Ca-Cb alkylimino herein means an alkyl-N= group in which the
alkyl means a previously mentioned alkyl group containing from a to b carbon atoms,
35 such as a methylimino group, an ethylimino group, a n-propylimino group, an ipropylimino
group, a n-butylimino group, an i-butylimino group or a s-butylimino group,
and those within the designated carbon atom range are selected.
The expression Ca-Cb alkoxyimino herein means an alkoxy-N= group in which the
alkoxy means a previously mentioned alkoxy group containing from a to b carbon atoms,
40 such as a methoxyimino group, an ethoxyimino group, a n-propyloxyimino group, an ipropyloxyimino
group or a n-butyloxyimino group, and those within the designated
carbon atom range are selected.
The expression Ca-Cb alkylcarbonyl herein means an alkyl-C(O)- group in which
the alkyl means a previously mentioned alkyl group containing from a to b carbon atoms,
45 such as an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a
valeryl group, an isovaleryl group, a 2-methylbutanoyl group, a pivaloyl group, a
hexanoyl group or a heptanoyl group, and those within the designated carbon atom
range are selected.
20
The expression Ca-Cb haloalkylcarbonyl herein means a haloalkyl-C(O)- group in
which the haloalkyl means a previously mentioned haloalkyl group containing from a to
b carbon atoms, such as a fluoroacetyl group, a chloroacetyl group, a difluoroacetyl
group, a dichloroacetyl group, a trifluoroacetyl group, a chlorodifluoroacetyl group, a
bromodifluoroacetyl group, a trichloroacetyl group, a pentafluoropropionyl 5 group, a
heptafluorobutanoyl group or a 3-chloro-2,2-dimethylpropanoyl group, and those within
the designated carbon atom range are selected.
The expression Ca-Cb cycloalkylcarbonyl herein means a cycloalkyl-C(O)- group in
which the cycloalkyl means a previously mentioned cycloalkyl group containing from a
10 to b carbon atoms, such as a cyclopropylcarbonyl group, a 2-methylcyclopropylcarbonyl
group or a cyclobutylcarbonyl group, and those within the designated carbon atom
range are selected.
The expression Ca-Cb alkoxycarbonyl herein means an alkyl-O-C(O)- group in
which the alkyl means a previously mentioned alkyl group containing from a to b carbon
15 atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, a npropyloxycarbonyl
group, an i-propyloxycarbonyl group, a n-butoxycarbonyl group, an ibutoxycarbonyl
group or a tert-butoxycarbonyl group, and those within the designated
carbon atom range are selected.
The expression Ca-Cb haloalkoxycarbonyl herein means a haloalkyl-O-C(O)-
20 group in which the haloalkyl means a previously mentioned haloalkyl group containing
from a to b carbon atoms, such as a chloromethoxycarbonyl group, a 2-
chloroethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-
trifluoroethoxycarbonyl group or a 2,2,2-trichloroethoxycarbonyl group, and those within
the designated carbon atom range are selected.
25 The expression Ca-Cb alkylaminocarbonyl herein means a carbamoyl group in
which either hydrogen atom is replaced by a previously mentioned alkyl group
containing from a to b carbon atoms, such as a methylcarbamoyl group, an
ethylcarbamoyl group, a n-propylcarbamoyl group, an i-propylcarbamoyl group, a nbutylcarbamoyl
group, an i-butylcarbamoyl group, a s-butylcarbamoyl group or a tert30
butylcarbamoyl group, and those within the designated carbon atom range are selected.
The expression Ca-Cb haloalkylaminocarbonyl herein means a carbamoyl group in
which either hydrogen atom is replaced by a previously mentioned haloalkyl group
containing from a to b carbon atoms, such as a 2-fluoroethylcarbamoyl group, a 2-
chloroethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group or a 2,2,2-
35 trifluoroethylcarbamoyl group, and those within the designated carbon atom range are
selected.
The expression di(Ca-Cb alkyl)aminocarbonyl herein means a carbamoyl group in
which both hydrogen atoms are replaced by previously mentioned alkyl groups
containing from a to b carbon atoms which may be identical with or different from each
40 other, such as an N,N-dimethylcarbamoyl group, an N-ethyl-N-methylcarbamoyl group,
an N,N-diethylcarbamoyl group, an N,N-di(n-propyl)carbamoyl group or an N,N-di(nbutyl)
carbamoyl group, and those within the designated carbon atom range are selected.
The expression Ca-Cb alkylaminosulfonyl herein means a sulfamoyl group in which
either hydrogen atom is replaced by a previously mentioned alkyl group containing from
45 a to b carbon atoms, such as a methylsulfamoyl group, an ethylsulfamoyl group, a npropylsulfamoyl
group, an i-propylsulfamoyl group, a n-butylsulfamoyl group, an ibutylsulfamoyl
group, a s-butylsulfamoyl group or a tert-butylsulfamoyl group, and those
within the designated carbon atom range are selected.
21
The expression di(Ca-Cb alkyl)aminosulfonyl herein means a sulfamoyl group in
which both hydrogen atoms are replaced by previously mentioned alkyl groups
containing from a to b carbon atoms which may be identical with or different from each
other, such as an N,N-dimethylsulfamoyl group, an N-ethyl-N-methylsulfamoyl group, an
N,N-diethylsulfamoyl group, an N,N-di(n-propyl)sulfamoyl group or an N,N-di(5 nbutyl)
sulfamoyl group, and those within the designated carbon atom range are selected.
The expression such as (Ca-Cb) alkyl optionally substituted with R5, (Ca-Cb) alkyl
optionally substituted with R14, (Ca-Cb) alkyl optionally substituted with R14a, (Ca-Cb) alkyl
optionally substituted with R19, (Ca-Cb) alkyl optionally substituted with R28, (Ca-Cb) alkyl
10 optionally substituted with R28a, (Ca-Cb) alkyl optionally substituted with R32or (Ca-Cb)
alkyl optionally substituted with R32a herein means a previously mentioned alkyl group
having from a to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are
optionally substituted with optional R5, R14, R14a, R19, R28, R28a, R32 or R32a, and those
within the designated carbon atom range are selected. When there are two or more
15 R5’s, R14’s, R14a’s, R19’s, R28’s, R28a’s, R32’s or R32a’s on a (Ca-Cb) alkyl group, each R5,
R14, R14a, R19, R28, R28a, R32 or R32a may be identical with or different from one another.
The expression such as (Ca-Cb) cycloalkyl optionally substituted with R5, (Ca-Cb)
cycloalkyl optionally substituted with R14, (Ca-Cb) cycloalkyl optionally substituted with
R14a, (Ca-Cb) cycloalkyl optionally substituted with R19, (Ca-Cb) cycloalkyl optionally
20 substituted with R28, (Ca-Cb) cycloalkyl optionally substituted with R28a or (Ca-Cb)
cycloalkyl optionally substituted with R32 herein means a previously mentioned
cycloalkyl group having from a to b carbon atoms in which hydrogen atom(s) on carbon
atom(s) in the ring moiety and/or in the side chain are optionally substituted with (Ca-Cb)
cycloalkyl optionally substituted with optional R5, R14, R14a, R19, R28, R28a or R32, and
25 those within the designated carbon atom range are selected. When there are two or
more R5’s, R14’s, R14a’s, R19’s, R28’s, R28a’s or R32’s on a (Ca-Cb) cycloalkyl group, each
R5, R14, R14a, R19, R28, R28a or R32 may be identical with or different from one another.
The expression such as (Ca-Cb) alkenyl optionally substituted with R5, (Ca-Cb)
alkenyl optionally substituted with R14, (Ca-Cb) alkenyl optionally substituted with R14a,
30 (Ca-Cb) alkenyl optionally substituted with R19, (Ca-Cb) alkenyl optionally substituted with
R28, (Ca-Cb) alkenyl optionally substituted with R28a or (Ca-Cb) alkenyl optionally
substituted with R32 herein means a previously mentioned alkenyl group having from a
to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally
substituted with optional R5, R14, R14a, R19, R28, R28a or R32, and those within the
35 designated carbon atom range are selected. When there are two or more R5’s, R14’s,
R14a’s, R19’s, R28’s, R28a’s or R32‘s on a (Ca-Cb) alkenyl group, each R5, R14, R14a, R19,
R28, R28a or R32 may be identical with or different from one another.
The expression such as (Ca-Cb) cycloalkenyl optionally substituted with R5, (Ca-Cb)
cycloalkenyl optionally substituted with R14, (Ca-Cb) cycloalkenyl optionally substituted
40 with R14a, (Ca-Cb) cycloalkenyl optionally substituted with R19, (Ca-Cb) cycloalkenyl
optionally substituted with R28, (Ca-Cb) cycloalkenyl optionally substituted with R28a or
(Ca-Cb) cycloalkenyl optionally substituted with R32 herein mean a previously mentioned
cycloalkenyl group having from a to b carbon atoms in which hydrogen atom(s) on
carbon atom(s) in the ring moiety and/or in the side chain are optionally substituted with
45 optional R5, R14, R14a, R19, R28, R28a or R32, and those within the designated carbon
atom range are selected. When there are two or more R5’s, R14’s, R14a’s, R19’s, R28’s,
R28a’s or R32’s on a (Ca-Cb) cycloalkenyl group, each R5, R14, R14a, R19, R28, R28a or R32
may be identical with or different from one another.
22
The expression such as (Ca-Cb) alkynyl optionally substituted with R5, (Ca-Cb)
alkynyl optionally substituted with R14, (Ca-Cb) alkynyl optionally substituted with R14a,
(Ca-Cb) alkynyl optionally substituted with R19, (Ca-Cb) alkynyl optionally substituted with
R28, (Ca-Cb) alkynyl optionally substituted with R28a or (Ca-Cb) alkynyl optionally
substituted with R32 herein means a previously mentioned alkynyl group having from 5 a
to b carbon atoms in which hydrogen atom(s) on carbon atom(s) are optionally
substituted with optional R5, R14, R14a, R19, R28, R28a or R32, and those within the
designated carbon atom range are selected. When there are two or more R5’s, R14’s,
R14a’s, R19’s, R28’s, R28a’s or R32’s on a (Ca-Cb) alkynyl group, each R5, R14, R14a, R19,
10 R28, R28a or R32 may be identical with or different from one another.
The expression such as “R8 may form, together with R8a, a C2-C7 alkylene chain to
form a 3 to 8-membered ring together with the nitrogen atom attached to R8 and R8a,
wherein the alkylene chain may contain an oxygen atom, sulfur atom or nitrogen atom”,
“R13 and R13a may form, together with each other, a C2-C7 alkylene chain to form a 3 to
15 8-membered ring together with the nitrogen atom attached to R13 and R13a, wherein the
alkylene chain may contain an oxygen atom, sulfur atom or nitrogen atom” or “R17 and
R17a may form, together with each other, a C2-C7 alkylene chain to form a 3 to 8-
membered ring together with the nitrogen atom attached to R17 and R17a, wherein the
alkylene chain may contain an oxygen atom, sulfur atom or nitrogen atom” is specifically
20 exemplified by aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one,
oxazolidine, oxazolidin-2-one, oxazolidine-2-thione, thiazolidine, thiazolidin-2-one,
thiazolidine-2-thione, imidazolidine, imidazolidin-2-one, imidazolidine-2-thione,
piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-one,
2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-
25 thiazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, thiomorpholine,
perhydropyrimidin-2-one, piperazine, homopiperidine, homopiperidin-2-one,
heptamethylenimine or the like, and those within the designated carbon atom range are
selected.
The expression “Rb3 may form, together with Rb2, a C4-C6 alkylene chain or a C4-
30 C6 alkenylene chain to form a 5 to 7-membered ring together with the carbon atom
attached to Rb3 and Rb2, wherein the alkylene chain or the alkenylene chain may contain
from 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms” is specifically exemplified by
thiazolidin-2-ylidene, 2,3-dihydrothiazol-2-ylidene, imidazolidin-2-ylidene, 2,3-
dihydroimidazol-2-ylidene, 2,3-dihydro-1,3,4-thiadiazol-2-ylidene, 1,2-dihydropyridin-2-
35 ylidene, 2,3-dihydropyridazin-3-ylidene, 1,2-dihydropyrazin-2-ylidene, 1,2-
dihydropyrimidin-2-ylidene, 6H-2,3-dihydro-1,3,4-thiadiazin-2-ylidene or the like, and
those within the designated carbon atom range are selected.
The expression “R7 may form, together with Ra, a C2-C6 alkylene chain or a C2-C6
alkenylene chain containing a double bond to form a 4 to 8-membered ring together with
40 the carbon atom attached to R7 and the nitrogen atom attached to Ra, wherein the
alkylene chain or the alkenylene chain may contain one or two oxygen atoms, sulfur
atoms or nitrogen atoms” is specifically exemplified by pyrrolidin-2-one, pyrrolidine-2-
thione, 1H-pyrrol-2(5H)-one, pyrrolidine-2,5-dione, pyrrolidin-2-imine, piperidin-2-one,
piperidine-2-thione, piperidin-2-imine, 5,6-dihydropyridin-2(1H)-one, 1,3-oxazinan-2-one,
45 1,3-oxazinane-2-thione, 1,3-oxazinan-4-one, 1,3-thiazinan-4-one, tetrahydropyrimidin-
4(1H)-one, piperidine-2,3-dione, piperidine-2,6-dione or the like, and those within the
designated carbon atom range are selected.
The expression “R8a may form, together with Ra, a C2-C5 alkylene chain to form a
23
5 to 8-membered ring together with the nitrogen atom attached to R8a and the nitrogen
atom attached to Ra, wherein the alkylene chain may contain an oxygen atom, a sulfur
atom or a nitrogen atom” is specifically exemplified by imidazolidin-2-one, imidazolidine-
2-thione, imidazolidin-2-imine, imidazolidine-2,4-dione, tetrahydropyrimidin-2(1H)-one,
tetrahydropyrimidine-2(1H)-thione, tetrahydropyrimidin-2(1H)-imine, 1,2,4-oxazinan-5 3-
one, 1,3,5-oxazinan-4-one, 1,3,5-thiazinan-4-one, 1,3,5-triazinan-2-one,
dihydropyrimidine-2,4(1H,3H)-dione or the like, and those within the designated carbon
atom range are selected.
As the scope of the substituent represented by R3 in the compounds which fall
10 within the present invention, the following sets may, for example, be mentioned.
R3I: a hydrogen atom, a halogen atom, C1-C6 alkyl.
R3II: a halogen atom, C1-C6 alkyl.
R3III: a halogen atom.
As the scope of the substituent represented by Ra in the compounds which fall
15 within the present invention, the following sets may, for example, be mentioned.
RaI: C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R5 [wherein R5 is -OR11,
and R11 is C1-C6 alkyl], -C(=NR8b)R7a [wherein R7a is a hydrogen atom or -C1-C6 alkyl,
R8b is -OR11, and R11 is C1-C6 alkyl], (C1-C6) alkyl optionally substituted with R5 [wherein
R5 is -C(=NOR11)R12, and each of R11 and R12 is independently C1-C6 alkyl], (C1-C6)
20 alkyl optionally substituted with R5 [wherein R5 is -Si(R9a)(R9b)R9, and each of R9, R9a
and R9b is independently C1-C6 alkyl].
RaII: (C1-C6) alkyl optionally substituted with R5 [wherein R5 is -OR11, and R11 is
C1-C6 alkyl].
RaIII: C1-C6 alkyl.
25 RaIV: -C(=NR8b)R7a [wherein R7a is a hydrogen atom or -C1-C6 alkyl, R8b is -OR11,
and R11 is C1-C6 alkyl].
RaV: (C1-C6) alkyl optionally substituted with R5 [wherein R5 is -C(=NOR11)R12, and
each of R11 and R12 is independently C1-C6 alkyl].
RaVI: (C1-C6) alkyl optionally substituted with R5 [wherein R5 is -Si(R9a)(R9b)R9,
30 and each of R9, R9a and R9b is indepedendently C1-C6 alkyl].
RaVII: (C1-C6) alkyl optionally substituted with R5 [wherein R5 is -S(O)rR11, R11 is
C1-C6 alkyl, and r is an integer of from 0 to 2].
RaVIII: (C1-C6) alkyl optionally substituted with R5 [wherein R5 is cyano].
RaIX: (C1-C6) alkyl optionally substituted with R5 [wherein R5 is C3-C8 cycloalkyl].
35 RaX: C2-C12 alkynyl.
As the scope of the substituent represented by Rb in the compounds which fall
within the present invention, the following sets may, for example, be mentioned.
RbI: -C(O)R7, -C(S)R7, -C(O)OR6a [wherein R6a is C1-C6 alkyl], -C(O)N(R8a)R8
[wherein R8 is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14 or C3-C8
40 cycloalkyl, R8a is a hydrogen atom or C1-C6 alkyl, and R14 is a halogen atom],
-C(S)N(R8a)R8 [wherein R8 is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14 or
C3-C8 cycloalkyl, R8a is a hydrogen atom or C1-C6 alkyl, and R14 is a halogen atom].
RbII: -C(S)R7.
RbIII: -C(O)R7.
45 RbIV: -C(O)OR6a [wherein R6a is C1-C6 alkyl].
RbV: -C(O)N(R8a)R8 [wherein R8 is C1-C6 alkyl, (C1-C6) alkyl optionally substituted
with R14or C3-C8 cycloalkyl, R8a is a hydrogen atom or C1-C6 alkyl, and R14 is a halogen
atom].
24
RbVI: -C(S)N(R8a)R8 [wherein R8 is C1-C6 alkyl, (C1-C6) alkyl optionally substituted
with R14or C3-C8 cycloalkyl, R8a is a hydrogen atom or C1-C6 alkyl, and R14 is a halogen
atom].
RbVII: Rb forms =C(Rb2)Rb3 together with Ra [wherein Rb2 is a hydrogen atom or
C1-C15 alkyl, Rb3 is -N(R8b)R8, R8 is -C(O)R12, R8b is C1-C15 alkyl or -OR11, R11 is C1-5 -C6
alkyl, and R12 is (C1-C6) alkyl optionally substituted with R14a].
As the scope of the substituent represented by R7 in the compounds which fall
within the present invention, the following sets may, for example, be mentioned.
R7I: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is -S(O)rR15, R15 is
10 C1-C6 alkyl, r is an integer of from 0 to 2], -C(=NOR11)R12 [wherein R11 is C1-C6 alkyl, R12
is (C1-C6) alkyl optionally substituted with R14a, R14a is -S(O)rR15, R15 is C1-C6 alkyl, and r
is an integer of from 0 to 2].
R7II: -C(=NOR11)R12 [wherein R11 is C1-C6 alkyl, R12 is (C1-C6) alkyl optionally
substituted with R14a, R14a is -S(O)rR15, R15 is C1-C6 alkyl, and r is an integer of from 0 to
15 2].
R7III: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is -S(O)rR15, R15 is
C1-C6 alkyl, and r is an integer of from 0 to 2].
R7IV: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is D1-82, D1-87,
D1-93 or D1-98, and r is an integer of from 0 to 2].
20 R7V: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is D1-82 or D1-93,
and r is an integer of from 0 to 2].
R7VI: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is D1-87 or D1-98].
R7VII: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is -S(O)rR15, R15 is
D1-32, and r is an integer of from 0 to 2].
25 R7VIII: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is -S(=NR17b)R15a
or -S(O)(=NR17b)R15a, R15a is C1-C6 alkyl, and R17b is cyano].
R7IX: (C1-C6) alkyl optionally substituted with R14 [wherein R14 is -C(O)N(R17a)R17,
R17 is (C1-C6) alkyl optionally substituted with R19 or -S(O)rR20, R17a is a hydrogen atom
or -C1-C6 alkyl, R19 is a halogen atom, R20 is C1-C6 alkyl, (C1-C6) alkyl optionally
30 substituted with R32, and R32 is a halogen atom].
The sets indicating the scope of each substituent in the compounds which fall
within the present invention may be combined arbitrarily to indicate the scope of the
compounds of the present invention. The scope of R3, Ra, Rb or R7 may be combined,
for example, as shown in Table 1. The combinations shown in Table 1 merely
35 exemplify the present invention, and the present invention is by no means restricted
thereto.
25
TABLE 1
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I Ra I Rb I R7 5 I
R3 I Ra I Rb I R7 II
R3 I Ra I Rb I R7 III
R3 I Ra I Rb I R7 IV
R3 I Ra I Rb I R7V
10 R3 I Ra I Rb I R7 VI
R3 I Ra I Rb I R7 VII
R3 I Ra I Rb I R7 VIII
R3 I Ra I Rb I R7 IX
R3 I Ra I Rb II R7 I
15 R3 I Ra I Rb II R7 II
R3 I Ra I Rb II R7 III
R3 I Ra I Rb II R7 IV
R3 I Ra I Rb II R7V
R3 I Ra I Rb II R7 VI
20 R3 I Ra I Rb II R7 VII
R3 I Ra I Rb II R7 VIII
R3 I Ra I Rb II R7 IX
R3 I Ra I Rb III R7 I
R3 I Ra I Rb III R7 II
25 R3 I Ra I Rb III R7 III
R3 I Ra I Rb III R7 IV
R3 I Ra I Rb III R7V
R3 I Ra I Rb III R7 VI
R3 I Ra I Rb III R7 VII
30 R3 I Ra I Rb III R7 VIII
R3 I Ra I Rb III R7 IX
R3 I Ra I Rb IV --
R3 I Ra I Rb V --
R3 I Ra I Rb VI --
35 R3 I Ra II Rb I R7 I
R3 I Ra II Rb I R7 II
R3 I Ra II Rb I R7 III
――――――――――――――
26
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I Ra II Rb I R7 5 IV
R3 I Ra II Rb I R7V
R3 I Ra II Rb I R7 VI
R3 I Ra II Rb I R7 VII
R3 I Ra II Rb I R7 VIII
10 R3 I Ra II Rb I R7 IX
R3 I Ra II Rb II R7 I
R3 I Ra II Rb II R7 II
R3 I Ra II Rb II R7 III
R3 I Ra II Rb II R7 IV
15 R3 I Ra II Rb II R7V
R3 I Ra II Rb II R7 VI
R3 I Ra II Rb II R7 VII
R3 I Ra II Rb II R7 VIII
R3 I Ra II Rb II R7 IX
20 R3 I Ra II Rb III R7 I
R3 I Ra II Rb III R7 II
R3 I Ra II Rb III R7 III
R3 I Ra II Rb III R7 IV
R3 I Ra II Rb III R7V
25 R3 I Ra II Rb III R7 VI
R3 I Ra II Rb III R7 VII
R3 I Ra II Rb III R7 VIII
R3 I Ra II Rb III R7 IX
R3 I Ra II Rb IV --
30 R3 I Ra II Rb V --
R3 I Ra II Rb VI --
R3 I Ra III Rb I R7 I
R3 I Ra III Rb I R7 II
R3 I Ra III Rb I R7 III
35 R3 I Ra III Rb I R7 IX
R3 I Ra III Rb I R7 IV
R3 I Ra III Rb I R7V
R3 I Ra III Rb I R7 VI
――――――――――――――
40
27
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I Ra III Rb I R7 5 VII
R3 I Ra III Rb I R7 VIII
R3 I Ra III Rb II R7 I
R3 I Ra III Rb II R7 II
R3 I Ra III Rb II R7 III
10 R3 I Ra III Rb II R7 IV
R3 I Ra III Rb II R7V
R3 I Ra III Rb II R7 VI
R3 I Ra III Rb II R7 VII
R3 I Ra III Rb II R7 VIII
15 R3 I Ra III Rb II R7 IX
R3 I Ra III Rb III R7 I
R3 I Ra III Rb III R7 II
R3 I Ra III Rb III R7 III
R3 I Ra III Rb III R7 IV
20 R3 I Ra III Rb III R7V
R3 I Ra III Rb III R7 VI
R3 I Ra III Rb III R7 VII
R3 I Ra III Rb III R7 VIII
R3 I Ra III Rb III R7 IX
25 R3 I Ra III Rb IV --
R3 I Ra III Rb V --
R3 I Ra III Rb VI --
R3 I Ra IV Rb I R7 I
R3 I Ra IV Rb I R7 II
30 R3 I Ra IV Rb I R7 III
R3 I Ra IV Rb I R7 IV
R3 I Ra IV Rb I R7V
R3 I Ra IV Rb I R7 VI
R3 I Ra IV Rb I R7 VII
35 R3 I Ra IV Rb I R7 VIII
R3 I Ra IV Rb I R7 IX
R3 I Ra IV Rb II R7 I
R3 I Ra IV Rb II R7 II
――――――――――――――
40
28
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I Ra IV Rb II R7 5 III
R3 I Ra IV Rb II R7 IV
R3 I Ra IV Rb II R7V
R3 I Ra IV Rb II R7 VI
R3 I Ra IV Rb II R7 VII
10 R3 I Ra IV Rb II R7 VIII
R3 I Ra IV Rb II R7 IX
R3 I Ra IV Rb III R7 I
R3 I Ra IV Rb III R7 II
R3 I Ra IV Rb III R7 III
15 R3 I Ra IV Rb III R7 IV
R3 I Ra IV Rb III R7V
R3 I Ra IV Rb III R7 VI
R3 I Ra IV Rb III R7 VII
R3 I Ra IV Rb III R7 VIII
20 R3 I Ra IV Rb III R7 IX
R3 I Ra IV Rb IV --
R3 I Ra IV Rb V --
R3 I Ra IV Rb VI --
R3 I RaV Rb I R7 I
25 R3 I RaV Rb I R7 II
R3 I RaV Rb I R7 III
R3 I RaV Rb I R7 IV
R3 I RaV Rb I R7V
R3 I RaV Rb I R7 VI
30 R3 I RaV Rb I R7 VII
R3 I RaV Rb I R7 VIII
R3 I RaV Rb I R7 IX
R3 I RaV Rb II R7 I
R3 I RaV Rb II R7 II
35 R3 I RaV Rb II R7 III
R3 I RaV Rb II R7 IV
R3 I RaV Rb II R7V
――――――――――――――
29
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I RaV Rb II R7 5 VI
R3 I RaV Rb II R7 VII
R3 I RaV Rb II R7 VIII
R3 I RaV Rb II R7 IX
R3 I RaV Rb III R7 I
10 R3 I RaV Rb III R7 II
R3 I RaV Rb III R7 III
R3 I RaV Rb III R7 IV
R3 I RaV Rb III R7V
R3 I RaV Rb III R7 VI
15 R3 I RaV Rb III R7 VII
R3 I RaV Rb III R7 VIII
R3 I RaV Rb III R7 IX
R3 I RaV Rb IV --
R3 I RaV RbV --
20 R3 I RaV Rb VI --
R3 I RaVI Rb I R7 I
R3 I RaVI Rb I R7 II
R3 I RaVI Rb I R7 III
R3 I RaVI Rb I R7 IV
25 R3 I RaVI Rb I R7V
R3 I RaVI Rb I R7 VI
R3 I RaVI Rb I R7 VII
R3 I RaVI Rb I R7 VIII
R3 I RaVI Rb I R7 IX
30 R3 I RaVI Rb II R7 I
R3 I RaVI Rb II R7 II
R3 I RaVI Rb II R7 III
R3 I RaVI Rb II R7 IV
R3 I RaVI Rb II R7V
35 R3 I RaVI Rb II R7 VI
R3 I RaVI Rb II R7 VII
R3 I RaVI Rb II R7 VIII
R3 I RaVI Rb II R7 IX
――――――――――――――
40
30
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I RaVI Rb III R7 5 I
R3 I RaVI Rb III R7 II
R3 I RaVI Rb III R7 III
R3 I RaVI Rb III R7 IV
R3 I RaVI Rb III R7V
10 R3 I RaVI Rb III R7 VI
R3 I RaVI Rb III R7 VII
R3 I RaVI Rb III R7 VIII
R3 I RaVI Rb III R7 IX
R3 I RaVI Rb IV --
15 R3 I RaVI Rb V --
R3 I RaVI Rb VI --
R3 I Ra VII Rb I R7 I
R3 I Ra VII Rb I R7 II
R3 I Ra VII Rb I R7 III
20 R3 I Ra VII Rb I R7 IV
R3 I Ra VII Rb I R7V
R3 I Ra VII Rb I R7 VI
R3 I Ra VII Rb I R7 VII
R3 I Ra VII Rb I R7 VIII
25 R3 I Ra VII Rb I R7 IX
R3 I Ra VII Rb II R7 I
R3 I Ra VII Rb II R7 II
R3 I Ra VII Rb II R7 III
R3 I Ra VII Rb II R7 IV
30 R3 I Ra VII Rb II R7V
R3 I Ra VII Rb II R7 VI
R3 I Ra VII Rb II R7 VII
R3 I Ra VII Rb II R7 VIII
R3 I Ra VII Rb II R7 IX
35 R3 I Ra VII Rb III R7 I
R3 I Ra VII Rb III R7 II
R3 I Ra VII Rb III R7 III
――――――――――――――
31
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I Ra VII Rb 5 III R7 IV
R3 I Ra VII Rb III R7V
R3 I Ra VII Rb III R7 VI
R3 I Ra VII Rb III R7 VII
R3 I Ra VII Rb III R7 VIII
10 R3 I Ra VII Rb III R7 IX
R3 I Ra VII Rb IV --
R3 I Ra VII Rb V --
R3 I Ra VII RbVI --
R3 I Ra VIII Rb I R7 I
15 R3 I Ra VIII Rb I R7 II
R3 I Ra VIII Rb I R7 III
R3 I Ra VIII Rb I R7 IV
R3 I Ra VIII Rb I R7V
R3 I Ra VIII Rb I R7 VI
20 R3 I Ra VIII Rb I R7 VII
R3 I Ra VIII Rb I R7 VIII
R3 I Ra VIII Rb I R7 IX
R3 I Ra VIII Rb II R7 I
R3 I Ra VIII Rb II R7 II
25 R3 I Ra VIII Rb II R7 III
R3 I Ra VIII Rb II R7 IV
R3 I Ra VIII Rb II R7V
R3 I Ra VIII Rb II R7 VI
R3 I Ra VIII Rb II R7 VII
30 R3 I Ra VIII Rb II R7 VIII
R3 I Ra VIII Rb II R7 IX
R3 I Ra VIII Rb III R7 I
R3 I Ra VIII Rb III R7 II
R3 I Ra VIII Rb III R7 III
35 R3 I Ra VIII Rb III R7 IV
R3 I Ra VIII Rb III R7V
R3 I Ra VIII Rb III R7 VI
――――――――――――――
32
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I Ra VIII Rb 5 III R7 VII
R3 I Ra VIII Rb III R7 VIII
R3 I Ra VIII Rb III R7 IX
R3 I Ra VIII Rb IV --
R3 I Ra VIII RbV --
10 R3 I Ra VIII RbVI --
R3 I Ra IX Rb I R7 I
R3 I Ra IX Rb I R7 II
R3 I Ra IX Rb I R7 III
R3 I Ra IX Rb I R7 IV
15 R3 I Ra IX Rb I R7V
R3 I Ra IX Rb I R7 VI
R3 I Ra IX Rb I R7 VII
R3 I Ra IX Rb I R7 VIII
R3 I Ra IX Rb I R7 IX
20 R3 I Ra IX Rb II R7 I
R3 I Ra IX Rb II R7 II
R3 I Ra IX Rb II R7 III
R3 I Ra IX Rb II R7 IV
R3 I Ra IX Rb II R7V
25 R3 I Ra IX Rb II R7 VI
R3 I Ra IX Rb II R7 VII
R3 I Ra IX Rb II R7 VIII
R3 I Ra IX Rb II R7 IX
R3 I Ra IX Rb III R7 I
30 R3 I Ra IX Rb III R7 II
R3 I Ra IX Rb III R7 III
R3 I Ra IX Rb III R7 IV
R3 I Ra IX Rb III R7V
R3 I Ra IX Rb III R7 VI
35 R3 I Ra IX Rb III R7 VII
R3 I Ra IX Rb III R7 VIII
R3 I Ra IX Rb III R7 IX
R3 I Ra IX Rb IV --
――――――――――――――
40
33
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 I Ra IX Rb V -5 -
R3 I Ra IX Rb VI --
R3 I RaX Rb I R7 I
R3 I RaX Rb I R7 II
R3 I RaX Rb I R7 III
10 R3 I RaX Rb I R7 IV
R3 I RaX Rb I R7V
R3 I RaX Rb I R7 VI
R3 I RaX Rb I R7 VII
R3 I RaX Rb I R7 VIII
15 R3 I RaX Rb I R7 IX
R3 I RaX Rb II R7 I
R3 I RaX Rb II R7 II
R3 I RaX Rb II R7 III
R3 I RaX Rb II R7 IV
20 R3 I RaX Rb II R7V
R3 I RaX Rb II R7 VI
R3 I RaX Rb II R7 VII
R3 I RaX Rb II R7 VIII
R3 I RaX Rb II R7 IX
25 R3 I RaX Rb III R7 I
R3 I RaX Rb III R7 II
R3 I RaX Rb III R7 III
R3 I RaX Rb III R7 IV
R3 I RaX Rb III R7V
30 R3 I RaX Rb III R7 VI
R3 I RaX Rb III R7 VII
R3 I RaX Rb III R7 VIII
R3 I RaX Rb III R7 IX
R3 I RaX Rb IV --
35 R3 I RaX RbV --
R3 I RaX Rb VI --
R3 II Ra I Rb I R7 I
――――――――――――――
34
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II Ra I Rb I R7 5 II
R3 II Ra I Rb I R7 III
R3 II Ra I Rb I R7 IV
R3 II Ra I Rb I R7V
R3 II Ra I Rb I R7 VI
10 R3 II Ra I Rb I R7 VII
R3 II Ra I Rb I R7 VIII
R3 II Ra I Rb I R7 IX
R3 II Ra I Rb II R7 I
R3 II Ra I Rb II R7 II
15 R3 II Ra I Rb II R7 III
R3 II Ra I Rb II R7 IV
R3 II Ra I Rb II R7V
R3 II Ra I Rb II R7 VI
R3 II Ra I Rb II R7 VII
20 R3 II Ra I Rb II R7 VIII
R3 II Ra I Rb II R7 IX
R3 II Ra I Rb III R7 I
R3 II Ra I Rb III R7 II
R3 II Ra I Rb III R7 III
25 R3 II Ra I Rb III R7 IV
R3 II Ra I Rb III R7V
R3 II Ra I Rb III R7 VI
R3 II Ra I Rb III R7 VII
R3 II Ra I Rb III R7 VIII
30 R3 II Ra I Rb III R7 IX
R3 II Ra I Rb IV --
R3 II Ra I Rb V --
R3 II Ra I Rb VI --
R3 II Ra II Rb I R7 I
35 R3 II Ra II Rb I R7 II
R3 II Ra II Rb I R7 III
R3 II Ra II Rb I R7 IV
――――――――――――――
35
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II Ra II Rb I R75 V
R3 II Ra II Rb I R7 VI
R3 II Ra II Rb I R7 VII
R3 II Ra II Rb I R7 VIII
R3 II Ra II Rb I R7 IX
10 R3 II Ra II Rb II R7 I
R3 II Ra II Rb II R7 II
R3 II Ra II Rb II R7 III
R3 II Ra II Rb II R7 IV
R3 II Ra II Rb II R7V
15 R3 II Ra II Rb II R7 VI
R3 II Ra II Rb II R7 VII
R3 II Ra II Rb II R7 VIII
R3 II Ra II Rb II R7 IX
R3 II Ra II Rb III R7 I
20 R3 II Ra II Rb III R7 II
R3 II Ra II Rb III R7 III
R3 II Ra II Rb III R7 IV
R3 II Ra II Rb III R7V
R3 II Ra II Rb III R7 VI
25 R3 II Ra II Rb III R7 VII
R3 II Ra II Rb III R7 VIII
R3 II Ra II Rb III R7 IX
R3 II Ra II Rb IV --
R3 II Ra II Rb V --
30 R3 II Ra II Rb VI --
R3 II Ra III Rb I R7 I
R3 II Ra III Rb I R7 II
R3 II Ra III Rb I R7 III
R3 II Ra III Rb I R7 IV
35 R3 II Ra III Rb I R7V
R3 II Ra III Rb I R7 VI
R3 II Ra III Rb I R7 VII
――――――――――――――
36
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II Ra III Rb I R7 5 VIII
R3 II Ra III Rb I R7 IX
R3 II Ra III Rb II R7 I
R3 II Ra III Rb II R7 II
R3 II Ra III Rb II R7 III
10 R3 II Ra III Rb II R7 IV
R3 II Ra III Rb II R7V
R3 II Ra III Rb II R7 VI
R3 II Ra III Rb II R7 VII
R3 II Ra III Rb II R7 VIII
15 R3 II Ra III Rb II R7 IX
R3 II Ra III Rb III R7 I
R3 II Ra III Rb III R7 II
R3 II Ra III Rb III R7 III
R3 II Ra III Rb III R7 IV
20 R3 II Ra III Rb III R7V
R3 II Ra III Rb III R7 VI
R3 II Ra III Rb III R7 VII
R3 II Ra III Rb III R7 VIII
R3 II Ra III Rb III R7 IX
25 R3 II Ra III Rb IV --
R3 II Ra III Rb V --
R3 II Ra III RbVI --
R3 II Ra IV Rb I R7 I
R3 II Ra IV Rb I R7 II
30 R3 II Ra IV Rb I R7 III
R3 II Ra IV Rb I R7 IV
R3 II Ra IV Rb I R7V
R3 II Ra IV Rb I R7 VI
R3 II Ra IV Rb I R7 VII
35 R3 II Ra IV Rb I R7 VIII
R3 II Ra IV Rb I R7 IX
R3 II Ra IV Rb II R7 I
R3 II Ra IV Rb II R7 II
――――――――――――――
40
37
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II Ra IV Rb II R7 5 III
R3 II Ra IV Rb II R7 IV
R3 II Ra IV Rb II R7V
R3 II Ra IV Rb II R7 VI
R3 II Ra IV Rb II R7 VII
10 R3 II Ra IV Rb II R7 VIII
R3 II Ra IV Rb II R7 IX
R3 II Ra IV Rb III R7 I
R3 II Ra IV Rb III R7 II
R3 II Ra IV Rb III R7 III
15 R3 II Ra IV Rb III R7 IV
R3 II Ra IV Rb III R7V
R3 II Ra IV Rb III R7 VI
R3 II Ra IV Rb III R7 VII
R3 II Ra IV Rb III R7 VIII
20 R3 II Ra IV Rb III R7 IX
R3 II Ra IV Rb IV --
R3 II Ra IV Rb V --
R3 II Ra IV RbVI --
R3 II RaV Rb I R7 I
25 R3 II RaV Rb I R7 II
R3 II RaV Rb I R7 III
R3 II RaV Rb I R7 IV
R3 II RaV Rb I R7V
R3 II RaV Rb I R7 VI
30 R3 II RaV Rb I R7 VII
R3 II RaV Rb I R7 VIII
R3 II RaV Rb I R7 IX
R3 II RaV Rb II R7 I
R3 II RaV Rb II R7 II
35 R3 II RaV Rb II R7 III
R3 II RaV Rb II R7 IV
R3 II RaV Rb II R7V
――――――――――――――
38
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II RaV Rb II R7 5 VI
R3 II RaV Rb II R7 VII
R3 II RaV Rb II R7 VIII
R3 II RaV Rb II R7 IX
R3 II RaV Rb III R7 I
10 R3 II RaV Rb III R7 II
R3 II RaV Rb III R7 III
R3 II RaV Rb III R7 IV
R3 II RaV Rb III R7V
R3 II RaV Rb III R7 VI
15 R3 II RaV Rb III R7 VII
R3 II RaV Rb III R7 VIII
R3 II RaV Rb III R7 IX
R3 II RaV Rb IV --
R3 II RaV Rb V --
20 R3 II RaV Rb VI --
R3 II RaVI Rb I R7 I
R3 II RaVI Rb I R7 II
R3 II RaVI Rb I R7 III
R3 II RaVI Rb I R7 IV
25 R3 II RaVI Rb I R7V
R3 II RaVI Rb I R7 VI
R3 II RaVI Rb I R7 VII
R3 II RaVI Rb I R7 VIII
R3 II RaVI Rb I R7 IX
30 R3 II RaVI Rb II R7 I
R3 II RaVI Rb II R7 II
R3 II RaVI Rb II R7 III
R3 II RaVI Rb II R7 IV
R3 II RaVI Rb II R7V
35 R3 II RaVI Rb II R7 VI
R3 II RaVI Rb II R7 VII
R3 II RaVI Rb II R7 VIII
R3 II RaVI Rb II R7 IX
――――――――――――――
40
39
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II RaVI Rb 5 III R7 I
R3 II RaVI Rb III R7 II
R3 II RaVI Rb III R7 III
R3 II RaVI Rb III R7 IV
R3 II RaVI Rb III R7V
10 R3 II RaVI Rb III R7 VI
R3 II RaVI Rb III R7 VII
R3 II RaVI Rb III R7 VIII
R3 II RaVI Rb III R7 IX
R3 II RaVI Rb IV --
15 R3 II RaVI Rb V --
R3 II RaVI RbVI --
R3 II Ra VII Rb I R7 I
R3 II Ra VII Rb I R7 II
R3 II Ra VII Rb I R7 III
20 R3 II Ra VII Rb I R7 IV
R3 II Ra VII Rb I R7V
R3 II Ra VII Rb I R7 VI
R3 II Ra VII Rb I R7 VII
R3 II Ra VII Rb I R7 VIII
25 R3 II Ra VII Rb I R7 IX
R3 II Ra VII Rb II R7 I
R3 II Ra VII Rb II R7 II
R3 II Ra VII Rb II R7 III
R3 II Ra VII Rb II R7 IV
30 R3 II Ra VII Rb II R7V
R3 II Ra VII Rb II R7 VI
R3 II Ra VII Rb II R7 VII
R3 II Ra VII Rb II R7 VIII
R3 II Ra VII Rb II R7 IX
35 R3 II Ra VII Rb III R7 I
R3 II Ra VII Rb III R7 II
R3 II Ra VII Rb III R7 III
――――――――――――――
40
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II Ra VII Rb 5 III R7 IV
R3 II Ra VII Rb III R7V
R3 II Ra VII Rb III R7 VI
R3 II Ra VII Rb III R7 VII
R3 II Ra VII Rb III R7 VIII
10 R3 II Ra VII Rb III R7 IX
R3 II Ra VII Rb IV --
R3 II Ra VII RbV --
R3 II Ra VII RbVI --
R3 II Ra VIII Rb I R7 I
15 R3 II Ra VIII Rb I R7 II
R3 II Ra VIII Rb I R7 III
R3 II Ra VIII Rb I R7 IV
R3 II Ra VIII Rb I R7V
R3 II Ra VIII Rb I R7 VI
20 R3 II Ra VIII Rb I R7 VII
R3 II Ra VIII Rb I R7 VIII
R3 II Ra VIII Rb I R7 IX
R3 II Ra VIII Rb II R7 I
R3 II Ra VIII Rb II R7 II
25 R3 II Ra VIII Rb II R7 III
R3 II Ra VIII Rb II R7 IV
R3 II Ra VIII Rb II R7V
R3 II Ra VIII Rb II R7 VI
R3 II Ra VIII Rb II R7 VII
30 R3 II Ra VIII Rb II R7 VIII
R3 II Ra VIII Rb II R7 IX
R3 II Ra VIII Rb III R7 I
R3 II Ra VIII Rb III R7 II
R3 II Ra VIII Rb III R7 III
35 R3 II Ra VIII Rb III R7 IV
R3 II Ra VIII Rb III R7V
R3 II Ra VIII Rb III R7 VI
R3 II Ra VIII Rb III R7 VII
――――――――――――――
40
41
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II Ra VIII Rb 5 III R7 VIII
R3 II Ra VIII Rb III R7 IX
R3 II Ra VIII Rb IV --
R3 II Ra VIII RbV --
R3 II Ra VIII RbVI --
10 R3 II Ra IX Rb I R7 I
R3 II Ra IX Rb I R7 II
R3 II Ra IX Rb I R7 III
R3 II Ra IX Rb I R7 IV
R3 II Ra IX Rb I R7V
15 R3 II Ra IX Rb I R7 VI
R3 II Ra IX Rb I R7 VII
R3 II Ra IX Rb I R7 VIII
R3 II Ra IX Rb I R7 IX
R3 II Ra IX Rb II R7 I
20 R3 II Ra IX Rb II R7 II
R3 II Ra IX Rb II R7 III
R3 II Ra IX Rb II R7 IV
R3 II Ra IX Rb II R7V
R3 II Ra IX Rb II R7 VI
25 R3 II Ra IX Rb II R7 VII
R3 II Ra IX Rb II R7 VIII
R3 II Ra IX Rb II R7 IX
R3 II Ra IX Rb III R7 I
R3 II Ra IX Rb III R7 II
30 R3 II Ra IX Rb III R7 III
R3 II Ra IX Rb III R7 IV
R3 II Ra IX Rb III R7V
R3 II Ra IX Rb III R7 VI
R3 II Ra IX Rb III R7 VII
35 R3 II Ra IX Rb III R7 VIII
R3 II Ra IX Rb III R7 IX
R3 II Ra IX Rb IV --
R3 II Ra IX Rb V --
R3 II Ra IX RbVI --
40 ――――――――――――――
42
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 II RaX Rb I R7 5 I
R3 II RaX Rb I R7 II
R3 II RaX Rb I R7 III
R3 II RaX Rb I R7 IV
R3 II RaX Rb I R7V
10 R3 II RaX Rb I R7 VI
R3 II RaX Rb I R7 VII
R3 II RaX Rb I R7 VIII
R3 II RaX Rb I R7 IX
R3 II RaX Rb II R7 I
15 R3 II RaX Rb II R7 II
R3 II RaX Rb II R7 III
R3 II RaX Rb II R7 IV
R3 II RaX Rb II R7V
R3 II RaX Rb II R7 VI
20 R3 II RaX Rb II R7 VII
R3 II RaX Rb II R7 VIII
R3 II RaX Rb II R7 IX
R3 II RaX Rb III R7 I
R3 II RaX Rb III R7 II
25 R3 II RaX Rb III R7 III
R3 II RaX Rb III R7 IV
R3 II RaX Rb III R7V
R3 II RaX Rb III R7 VI
R3 II RaX Rb III R7 VII
30 R3 II RaX Rb III R7 VIII
R3 II RaX Rb III R7 IX
R3 II RaX Rb IV --
R3 II RaX Rb V --
R3 II RaX Rb VI --
35 R3 III Ra I Rb I R7 I
R3 III Ra I Rb I R7 II
R3 III Ra I Rb I R7 III
――――――――――――――
43
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 III Ra I Rb I R7 5 IV
R3 III Ra I Rb I R7V
R3 III Ra I Rb I R7 VI
R3 III Ra I Rb I R7 VII
R3 III Ra I Rb I R7 VIII
10 R3 III Ra I Rb I R7 IX
R3 III Ra I Rb II R7 I
R3 III Ra I Rb II R7 II
R3 III Ra I Rb II R7 III
R3 III Ra I Rb II R7 IV
15 R3 III Ra I Rb II R7V
R3 III Ra I Rb II R7 VI
R3 III Ra I Rb II R7 VII
R3 III Ra I Rb II R7 VIII
R3 III Ra I Rb II R7 IX
20 R3 III Ra I Rb III R7 I
R3 III Ra I Rb III R7 II
R3 III Ra I Rb III R7 III
R3 III Ra I Rb III R7 IV
R3 III Ra I Rb III R7V
25 R3 III Ra I Rb III R7 VI
R3 III Ra I Rb III R7 VII
R3 III Ra I Rb III R7 VIII
R3 III Ra I Rb III R7 IX
R3 III Ra I Rb IV --
30 R3 III Ra I Rb V --
R3 III Ra I Rb VI --
R3 III Ra II Rb I R7 I
R3 III Ra II Rb I R7 II
R3 III Ra II Rb I R7 III
35 R3 III Ra II Rb I R7 IV
R3 III Ra II Rb I R7V
R3 III Ra II Rb I R7 VI
――――――――――――――
44
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 III Ra II Rb I R7 5 VII
R3 III Ra II Rb I R7 VIII
R3 III Ra II Rb I R7 IX
R3 III Ra II Rb II R7 I
R3 III Ra II Rb II R7 II
10 R3 III Ra II Rb II R7 III
R3 III Ra II Rb II R7 IV
R3 III Ra II Rb II R7V
R3 III Ra II Rb II R7 VI
R3 III Ra II Rb II R7 VII
15 R3 III Ra II Rb II R7 VIII
R3 III Ra II Rb II R7 IX
R3 III Ra II Rb III R7 I
R3 III Ra II Rb III R7 II
R3 III Ra II Rb III R7 III
20 R3 III Ra II Rb III R7 IV
R3 III Ra II Rb III R7V
R3 III Ra II Rb III R7 VI
R3 III Ra II Rb III R7 VII
R3 III Ra II Rb III R7 VIII
25 R3 III Ra II Rb III R7 IX
R3 III Ra II Rb IV --
R3 III Ra II Rb V --
R3 III Ra II RbVI --
R3 III Ra III Rb I R7 I
30 R3 III Ra III Rb I R7 II
R3 III Ra III Rb I R7 III
R3 III Ra III Rb I R7 IV
R3 III Ra III Rb I R7V
R3 III Ra III Rb I R7 VI
35 R3 III Ra III Rb I R7 VII
R3 III Ra III Rb I R7 VIII
R3 III Ra III Rb I R7 IX
R3 III Ra III Rb II R7 I
――――――――――――――
40
45
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 III Ra III Rb 5 II R7 II
R3 III Ra III Rb II R7 III
R3 III Ra III Rb II R7 IV
R3 III Ra III Rb II R7V
R3 III Ra III Rb II R7 VI
10 R3 III Ra III Rb II R7 VII
R3 III Ra III Rb II R7 VIII
R3 III Ra III Rb II R7 IX
R3 III Ra III Rb III R7 I
R3 III Ra III Rb III R7 II
15 R3 III Ra III Rb III R7 III
R3 III Ra III Rb III R7 IV
R3 III Ra III Rb III R7V
R3 III Ra III Rb III R7 VI
R3 III Ra III Rb III R7 VII
20 R3 III Ra III Rb III R7 VIII
R3 III Ra III Rb III R7 IX
R3 III Ra III Rb IV --
R3 III Ra III RbV --
R3 III Ra III RbVI --
25 R3 III Ra IV Rb I R7 I
R3 III Ra IV Rb I R7 II
R3 III Ra IV Rb I R7 III
R3 III Ra IV Rb I R7 IV
R3 III Ra IV Rb I R7V
30 R3 III Ra IV Rb I R7 VI
R3 III Ra IV Rb I R7 VII
R3 III Ra IV Rb I R7 VIII
R3 III Ra IV Rb I R7 IX
R3 III Ra IV Rb II R7 I
35 R3 III Ra IV Rb II R7 II
R3 III Ra IV Rb II R7 IV
R3 III Ra IV Rb II R7V
――――――――――――――
46
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 III Ra IV Rb 5 II R7 VI
R3 III Ra IV Rb II R7 III
R3 III Ra IV Rb II R7 VII
R3 III Ra IV Rb II R7 VIII
R3 III Ra IV Rb II R7 IX
10 R3 III Ra IV Rb III R7 I
R3 III Ra IV Rb III R7 II
R3 III Ra IV Rb III R7 III
R3 III Ra IV Rb III R7 IV
R3 III Ra IV Rb III R7V
15 R3 III Ra IV Rb III R7 VI
R3 III Ra IV Rb III R7 VII
R3 III Ra IV Rb III R7 VIII
R3 III Ra IV Rb III R7 IX
R3 III Ra IV Rb IV --
20 R3 III Ra IV RbV --
R3 III Ra IV RbVI --
R3 III RaV Rb I R7 I
R3 III RaV Rb I R7 II
R3 III RaV Rb I R7 III
25 R3 III RaV Rb I R7 IV
R3 III RaV Rb I R7V
R3 III RaV Rb I R7 VI
R3 III RaV Rb I R7 VII
R3 III RaV Rb I R7 VIII
30 R3 III RaV Rb I R7 IX
R3 III RaV Rb II R7 I
R3 III RaV Rb II R7 II
R3 III RaV Rb II R7 III
R3 III RaV Rb II R7 IV
35 R3 III RaV Rb II R7V
R3 III RaV Rb II R7 VI
R3 III RaV Rb II R7 VII
――――――――――――――
47
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 III RaV Rb II R7 5 VIII
R3 III RaV Rb II R7 IX
R3 III RaV Rb III R7 I
R3 III RaV Rb III R7 II
R3 III RaV Rb III R7 III
10 R3 III RaV Rb III R7 IV
R3 III RaV Rb III R7V
R3 III RaV Rb III R7 VI
R3 III RaV Rb III R7 VII
R3 III RaV Rb III R7 VIII
15 R3 III RaV Rb III R7 IX
R3 III RaV Rb IV --
R3 III RaV Rb V --
R3 III RaV RbVI --
R3 III RaVI Rb I R7 I
20 R3 III RaVI Rb I R7 II
R3 III RaVI Rb I R7 III
R3 III RaVI Rb I R7 IV
R3 III RaVI Rb I R7V
R3 III RaVI Rb I R7 VI
25 R3 III RaVI Rb I R7 VII
R3 III RaVI Rb I R7 VIII
R3 III RaVI Rb I R7 IX
R3 III RaVI Rb II R7 I
R3 III RaVI Rb II R7 II
30 R3 III RaVI Rb II R7 III
R3 III RaVI Rb II R7 IV
R3 III RaVI Rb II R7V
R3 III RaVI Rb II R7 VI
R3 III RaVI Rb II R7 VII
35 R3 III RaVI Rb II R7 VIII
R3 III RaVI Rb II R7 IX
R3 III RaVI Rb III R7 I
R3 III RaVI Rb III R7 II
――――――――――――――
40
48
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 III RaVI Rb 5 III R7 III
R3 III RaVI Rb III R7 IV
R3 III RaVI Rb III R7V
R3 III RaVI Rb III R7 VI
R3 III RaVI Rb III R7 VII
10 R3 III RaVI Rb III R7 VIII
R3 III RaVI Rb III R7 IX
R3 III RaVI Rb IV --
R3 III RaVI RbV --
R3 III RaVI RbVI --
15 R3 III Ra VII Rb I R7 I
R3 III Ra VII Rb I R7 II
R3 III Ra VII Rb I R7 III
R3 III Ra VII Rb I R7 IV
R3 III Ra VII Rb I R7V
20 R3 III Ra VII Rb I R7 VI
R3 III Ra VII Rb I R7 VII
R3 III Ra VII Rb I R7 VIII
R3 III Ra VII Rb I R7 IX
R3 III Ra VII Rb II R7 I
25 R3 III Ra VII Rb II R7 II
R3 III Ra VII Rb II R7 III
R3 III Ra VII Rb II R7 IV
R3 III Ra VII Rb II R7V
R3 III Ra VII Rb II R7 VI
30 R3 III Ra VII Rb II R7 VII
R3 III Ra VII Rb II R7 VIII
R3 III Ra VII Rb II R7 IX
R3 III Ra VII Rb III R7 I
R3 III Ra VII Rb III R7 II
35 R3 III Ra VII Rb III R7 III
R3 III Ra VII Rb III R7 IV
R3 III Ra VII Rb III R7V
――――――――――――――
49
TABLE 1 (continued)
――――――――――――――
R3 Ra Rb R7
――――――――――――――
R3 III Ra VII Rb 5 III R7 VI
R3 III Ra VII Rb III R7 VII
R3 III Ra VII Rb III R7 VIII
R3 III Ra VII Rb III R7 IX
R3 III Ra VII Rb IV --
10 R3 III Ra VII RbV --
R3 III Ra VII RbVI --
R3 III Ra VIII Rb I R7 I
R3 III Ra VIII Rb I R7 II
R3 III Ra VIII Rb I R7 III
15 R3 III Ra VIII Rb I R7 IV
R3 III Ra VIII Rb I R7V
R3 III Ra VIII Rb I R7 VI
R3 III Ra VIII Rb I R7 VII
R3 III Ra VIII Rb I R7 VIII
20 R3 III Ra VIII Rb I R7 IX
R3 III Ra VIII Rb II R7 I
R3 III Ra VIII Rb II R7 II
R3 III Ra VIII Rb II R7 III
R3 III Ra VIII Rb II R7 IV
25 R3 III Ra VIII Rb II R7V
R3 III Ra VIII Rb II R7 VI
R3 III Ra VIII Rb II R7 VII
R3 III Ra VIII Rb II R7 VIII
R3 III Ra VIII Rb II R7 IX
30 R3 III Ra VIII Rb III R7 I
R3 III Ra VIII Rb III R7 II
R3 III Ra VIII Rb III R7 III
R3 III Ra VIII Rb III R7 IV
R3 III Ra VIII Rb III R7V
35 R3 III Ra VIII Rb III R7 VI
R3 III Ra VIII Rb III R7 VII
R3 III Ra VIII Rb III R7 VIII
R3 III Ra VIII Rb III R7 IX
――――――――――――――

CLAIMS
1. A pyrazole derivative represented by the formula (1) or a salt thereof:
wherein A1 is -N(-O)m2 or -CR1,
each of R1 and R3 is independently a hydrogen atom, a halogen atom, cyano, nitro,
-OH, -SH, -NH2, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28a, C3-5 -C8
cycloalkyl, (C3-C8) cycloalkyl optionally substituted with R28a, C2-C6 alkenyl, (C2-C6)
alkenyl optionally substituted with R28a, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R28a, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted
with R28a, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6
10 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6
alkylcarbonyl, C3-C8 cycloalkylcarbonyl, C1-C6 haloalkylcarbonyl, C3-C8
halocycloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkoxycarbonyl, C1-C6
alkylaminosulfonyl, di(C1-C6 alkyl)aminosulfonyl, C1-C6 alkylamino or di(C1-C6
alkyl)amino,
15 R2 is a halogen atom, cyano, nitro, -OH, -SH, -NH2, C1-C6 alkyl, (C1-C6) alkyl optionally
substituted with R28a, C3-C8 cycloalkyl, (C3-C8) cycloalkyl optionally substituted with
R28a, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R28a, C3-C8 cycloalkenyl,
(C3-C8) cycloalkenyl optionally substituted with R28a, C2-C6 alkynyl, (C2-C6) alkynyl
optionally substituted with R28a, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6
20 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6
haloalkylsulfonyl, C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl, C1-C6
haloalkylcarbonyl, C3-C8 halocycloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6
haloalkoxycarbonyl, C1-C6 alkylaminosulfonyl, di(C1-C6 alkyl)aminosulfonyl, C1-C6
alkylamino or di(C1-C6 alkyl)amino, provided that when n is an integer of at least 2,
25 each R2 may be identical with or different from one another,
R4 is a hydrogen atom, a halogen atom, cyano, nitro, -OH, -SH, -NH2, C1-C6 alkyl, (C1-
C6) alkyl optionally substituted with R28a, C3-C8 cycloalkyl, (C3-C8) cycloalkyl optionally
substituted with R28a, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R28a, C3-
C8 cycloalkenyl, (C3-C8) cycloalkenyl optionally substituted with R28a, C2-C6 alkynyl,
30 (C2-C6) alkynyl optionally substituted with R28a, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6
alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6
haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl,
C1-C6 haloalkylcarbonyl, C3-C8 halocycloalkylcarbonyl, C1-C6 alkylamino or di(C1-C6
alkyl)amino,
35 Ra is a hydrogen atom, cyano, C1-C15 alkyl, (C1-C15) alkyl optionally substituted with R5,
C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R5, C2-C15 alkenyl, (C2-
C15) alkenyl optionally substituted with R5, C3-C12 cycloalkenyl, (C3-C15) cycloalkenyl
optionally substituted with R5, C2-C12 alkynyl, (C2-C15) alkynyl optionally substituted
A1 N
N
N
R3 N
R4
(R2)n
Ra
Rb
(O)m1
(1)
281
with R5, -OR6, -S(O)rR6, -C(O)R7a, -C(O)OR6a, -NR8cR8d, -C(=NR8b)R7a, -S(O)rN(R8a)R8,
phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to
D1-99,
Rb is -S(O)rR6, -C(O)R7, -C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(S)OR6a, -C(S)SR6a, -
C(O)N(R8a)R8, -C(S)N(R8a)R8, -C(O)N(R8b)N(R8a)R8, -C(O)N(R8a)OR6a, -C(=NR8b)OR6a5 ,
-C(=NR8b)SR6a, -C(=NR8b)N(R8a)R8, -C(=NR8b)R7, D1-49, D1-51, D1-53, D1-59, D1-61
or D1-63 or Rb may form =C(Rb2)Rb3 together with Ra,
Rb2 is a hydrogen atom, C1-C15 alkyl or -S(O)rR6,
Rb3 is (C1-C15) alkyl optionally substituted with R14, -OR6, -S(O)rR6 or -N(R8b)R8, or Rb3
10 may form, together with Rb2, a C4-C6 alkylene chain or a C4-C6 alkenylene chain to
form a 5 to 7-membered ring together with the carbon atom attached to Rb3 and Rb2,
wherein the alkylene chain or the alkenylene chain may contain from 1 to 3 oxygen
atoms, sulfur atoms or nitrogen atoms and may optionally be substituted with a
halogen atom, a cyano group, a nitro group, C1-C6 alkyl, (C1-C12) alkyl optionally
15 substituted with R14, -S(O)rR6, -C(O)R7, -C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(S)OR6a,
-C(S)SR6a, -C(O)N(R8a)R8, -C(S)N(R8a)R8, -C(O)N(R8b)N(R8a)R8, -C(O)N(R8a)OR6,
-C(=NR8b)OR6a, -C(=NR8b)SR6a, -C(=NR8b)N(R8a)R8, -C(=NR8b)R7, phenyl, phenyl
substituted with (Z)q, an oxo group, a thioxo group, =NR8b or a C1-C6 alkylidene group,
R5 is a halogen atom, cyano, nitro, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally
20 substituted with R14, -OH, -OR11, -SH, -S(O)rR11, -C(O)R12, -C(O)OR11a, -C(O)SR6a,
-C(S)OR6a, -C(S)SR6a, -C(O)N(R13a)R13, -C(S)N(R13a)R13, -C(=NOH)R12,
-C(=NOR11)R12, -N(R13a)R13, -Si(R9a)(R9b)R9, -P(O)(OR10)2, -P(S)(OR10)2, phenyl,
phenyl substituted with (Z3)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to D1-99,
each of R6 and R6a is independently C1-C15 alkyl, (C1-C15) alkyl optionally substituted
25 with R14, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14, C2-C15
alkenyl, (C2-C15) alkenyl optionally substituted with R14, C3-C15 cycloalkenyl, (C3-C15)
cycloalkenyl optionally substituted with R14, C2-C15 alkynyl, (C2-C15) alkynyl optionally
substituted with R14, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl
substituted with (Z)q or D1-1 to D1-99,
30 R7 is a hydrogen atom, C1-C15 alkyl, (C1-C15) alkyl optionally substituted with R14, C3-
C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14, C2-C15 alkenyl, (C2-
C15) alkenyl optionally substituted with R14, C3-C15 cycloalkenyl, (C3-C15) cycloalkenyl
optionally substituted with R14, C2-C15 alkynyl, (C2-C15) alkynyl optionally substituted
with R14, -C(O)R12, -C(O)OR11, -C(O)N(R13a)R13, -C(S)N(R13a)R13, -C(=NOH)R12,
35 -C(=NOR11)R12, -C{=NN(R13a)R13}R12, phenyl, phenyl substituted with (Z)q, naphthyl,
naphthyl substituted with (Z)q or D1-1 to D1-99, or R7 may form, together with Ra, a C2-
C6 alkylene chain or a C2-C6 alkenylene chain containing a double bond to form a 4 to
8-membered ring together with the carbon atom attached to R7 and the nitrogen atom
attached to Ra, wherein the alkylene chain or the alkenylene chain may contain one or
40 two oxygen atoms, sulfur atoms or nitrogen atoms and may optionally be substituted
with a halogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with
R14, -OH, -OR11, -SH, -S(O)rR11, an oxo group, a thioxo group, =NR8b or a C1-C6
alkylidene group,
R7a is a hydrogen atom or R6a,
45 R8 is a hydrogen atom, cyano, R6a, -S(O)rR11, -C(O)R12, -C(O)OR11a, -C(O)N(R13a)R13,
-C(S)N(R13a)R13, -C(=NOH)R12, -C(=NOR11)R12, -S(O)2N(R13a)R13, phenyl, phenyl
substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to D1-99, or R8
282
may form, together with R8a, a C2-C7 alkylene chain to form a 3 to 8-membered ring
together with the nitrogen atom attached to R8 and R8a, wherein the alkylene chain
may contain an oxygen atom, a sulfur atom or a nitrogen atom and may optionally be
substituted with a halogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl optionally substituted
with R14, phenyl, phenyl substituted with (Z)q, an oxo group or a thioxo group, or 5 R8
may form =C(R8f)R8e together with R8a,
R8a is a hydrogen atom, cyano, C1-C15 alkyl, (C1-C15) alkyl optionally substituted with
R14a, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14a, C2-C15
alkenyl, (C2-C15) alke or nyl optionally substituted with R14a, C3-C15 cycloalkenyl, (C3-
10 C15) cycloalkenyl optionally substituted with R14a, C2-C15 alkynyl or (C2-C15) alkynyl
optionally substituted with R14a, or R8a may form, together with Ra, a C2-C5 alkylene
chain to form a 5 to 8-membered ring together with the nitrogen atom attached to R8a
and the nitrogen atom attached to Ra, wherein the alkylene chain may contain an
oxygen atom, a sulfur atom or a nitrogen atom and may optionally be substituted with a
15 halogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14,
-OH, -OR11, -SH, -S(O)rR11, an oxo group, a thioxo group or =NR8b,
R8b is a hydrogen atom, cyano, nitro, C1-C15 alkyl, (C1-C15) alkyl optionally substituted
with R14, C3-C15 cycloalkyl, (C3-C15) cycloalkyl optionally substituted with R14, C2-C15
alkenyl, (C2-C15) alkenyl optionally substituted with R14, C3-C15 cycloalkenyl, (C3-C15)
20 cycloalkenyl optionally substituted with R14, C2-C15 alkynyl, (C2-C15) alkynyl optionally
substituted with R14, -OR11, -S(O)rR11, -C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13,
-C(S)N(R13a)R13 or -S(O)2N(R13a)R13,
each of R8c and R8d is independently a hydrogen atom, C1-C6 alkyl, -S(O)rR11,
-C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13 or -C(S)N(R13a)R13,
25 R8e is a hydrogen atom, C1-C15 alkyl or -S(O)rR11,
R8f is C1-C15 alkyl, (C1-C15) alkyl optionally substituted with R14, -OR11, -S(O)rR11,
-N(R13a)R13, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl substituted with
(Z)q or or D1-1 to D1-99,
each of R9, R9a and R9b is independently C1-C6 alkyl,
30 R10 is a hydrogen atom or C1-C6 alkyl,
each of R11 and R11a is independently C1-C6 alkyl, (C1-C6) alkyl optionally substituted
with R14a, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R14a, C3-C8
cycloalkenyl, (C3-C8) cycloalkenyl optionally substituted with R14a, C2-C6 alkynyl, (C2-
C6) alkynyl optionally substituted with R14a, C3-C8 cycloalkyl, (C3-C8) cycloalkyl
35 optionally substituted with R14a, -Si(R9a)(R9b)R9, phenyl, phenyl substituted with (Z)q,
naphthyl, naphthyl substituted with (Z)q or or D1-1 to D1-99,
R12 is a hydrogen atom, R11a, -C(O)R16, -C(=NOH)R16, -C(=NOR15)R16, phenyl, phenyl
substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or or D1-1 to D1-99,
each of R13 and R13a is independently a hydrogen atom, R11a, -S(O)rR15, -C(O)OR15a,
40 -C(O)R16, -C(O)N(R17a)R17, -C(S)N(R17a)R17, -S(O)2N(R17a)R17, phenyl, phenyl
substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or or D1-1 to D1-99, or
R13 and R13a may form, together with each other, a C2-C7 alkylene chain to form a 3 to
8-membered ring together with the nitrogen atom attached to R13 and R13a, wherein the
alkylene chain may contain an oxygen atom, a sulfur atom or a nitrogen atom and may
45 optionally be substituted with a halogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R14, phenyl, phenyl substituted with (Z)q, an oxo group or a
thioxo group,
283
each of R14 and R14a is independently a halogen atom, cyano, nitro, C3-C8 cycloalkyl,
(C3-C8) cycloalkyl optionally substituted with R19, -OH, -OR15, -SH, -S(O)rR15,
-S(=NR17b)R15a, -S(O)(=NR17b)R15a, -C(O)OH, -C(O)OR15a, -C(O)SR15a, -C(S)OR15a,
-C(S)SR15a, -C(O)R16, -C(O)N(R17a)R17, -C(S)N(R17a)R17, -N(R17a)R17, -C(=NOH)R16,
-C(=NOR15)R16, -ON=C(R16a)R16, -S(O)2N(R17a)R17, -Si(R9a)(R9b)R9, -P(O)(OR10)5 2,
-P(S)(OR10)2, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl substituted with
(Z)q or D1-1 to D1-99,
each of R15 and R15a is independently cyano, C1-C6 alkyl, (C1-C6) alkyl optionally
substituted with R19, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with R19, C2-
10 C6 alkynyl, (C2-C6) alkynyl optionally substituted with R19, C3-C8 cycloalkyl, (C3-C8)
cycloalkyl optionally substituted with R19, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R19, -S(O)rR20, -C(O)OR20a, -C(O)R21, -C(O)N(R22a)R22,
-C(S)N(R22a)R22, phenyl, phenyl substituted with (Z)q2, naphthyl, naphthyl substituted
with (Z)q or D1-1 to D1-99,
15 each of R16 and R16a is independently a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R19, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
R19, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R19, C3-C8 cycloalkyl, (C3-
C8) cycloalkyl optionally substituted with R19, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R19, -C(O)R21, phenyl, phenyl substituted with (Z)q, naphthyl,
20 naphthyl substituted with (Z)q or D1-1 to D1-99,
each of R17 and R17a is independently a hydrogen atom, cyano, C1-C6 alkyl, (C1-C6)
alkyl optionally substituted with R19, C2-C6 alkenyl, (C2-C6) alkenyl optionally
substituted with R19, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R19, C3-
C8 cycloalkyl, (C3-C8) cycloalkyl optionally substituted with R19, C3-C8 cycloalkenyl, (C3-
25 C8) cycloalkenyl optionally substituted with R19, -CHO, -S(O)rR20, -C(O)R21, -C(O)OR20a,
-C(O)N(R22a)R22, -C(S)N(R22a)R22 or -S(O)2N(R22a)R22, or R17 and R17a may form,
together with each other, a C2-C7 alkylene chain to form a 3 to 8-membered ring
together with the nitrogen atom attached to R17 and R17a, wherein the alkylene chain
may contain an oxygen atom, a sulfur atom or a nitrogen atom and may optionally be
30 substituted with a halogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl optionally substituted
with R14, phenyl, phenyl substituted with (Z)q, an oxo group or a thioxo group,
R17b is a hydrogen atom, cyano, nitro, -OR20, -S(O)rR20, -C(O)OR20a, -C(O)R21,
-C(O)N(R22a)R22, -C(S)N(R22a)R22 or -S(O)2N(R22a)R22,
R19 is a halogen atom, cyano, C3-C8 cycloalkyl, -OR20, -S(O)rR20, -C(O)OR20a,
35 -C(O)N(R22a)R22, -C(S)N(R22a)R22, -C(=NOR20)R21, -Si(R9a)(R9b)R9, phenyl, phenyl
substituted with (Z)q, naphthyl, naphthyl substituted with (Z)q or D1-1 to D1-99,
each of R20 and R21 is independently a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R32, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
R32, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R32, C3-C8 cycloalkyl, (C3-
40 C8) cycloalkyl optionally substituted with R32, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R32, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl
substituted with (Z)q or D1-1 to D1-99,
each of R20a, R22 and R22a is independently a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl
optionally substituted with R32, C2-C6 alkenyl, (C2-C6) alkenyl optionally substituted with
45 R32, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with R32, C3-C8 cycloalkyl, (C3-
C8) cycloalkyl optionally substituted with R32, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R32, phenyl, phenyl substituted with (Z)q, naphthyl, naphthyl
284
substituted with (Z)q or D1-1 to D1-99,
D1-1 to D1-99 are rings represented by the following structures, respectively,
D1-1 D1-3 D1-4
D1-18 D1-19
D1-24 D1-25
D1-26 D1-27
D1-28 D1-29 D1-30
N
N
N
N
S
N
N
O
N
N N
N
N
N
N N
N
N N
N
N
N
N
N
N
N
N
N
N N
N
N
O
(X1)g4 X1a
(X1)g2 X1a
(X1)g3
(X1)g1
D1-2
S
(X1)g1 (X1)g1
D1-5
O
N
(X1)g2
D1-6
S
N
(X1)g2
D1-7
N
N
(X1)g1
D1-8
N N
X1a
(X1)g2
D1-9
N
O
(X1)g2
D1-10
N
S
(X1)g2
D1-11
N N
(X1)g1
D1-12
N
N
X1a
(X1)g2
D1-13
N
S
N
(X1)g3
D1-14
N
N
O
(X1)g3
D1-15
N
N
S
(X1)g3
D1-16
O
N
N
D1-17
S
N
N
(X1)g3 (X1)g3 (X1)g3 (X1)g3
D1-20
N N
N
(X1)g2
D1-21
N
N
N
X1a
(X1)g3
D1-22
N
N
N
(X1)g2
D1-23
N
N N
X1a
(X1)g3
(X1)g2
(X1)g3
X1a
(X1)g3 X1a
(X1)g3
285
D1-33
N
(X1)g4
D1-42
N
N
N
N (X1)g3
N
N N
N
D1-31
X1a
(O)m3
D1-35
N
N
(X1)g1
D1-36
N
N
(X1)g1
D1-39
N
N
(X1)g1
D1-40
N
N
N
(X1)g2
D1-41
N
N
N
(X1)g2
D1-34
N
(X1)g4
D1-32
N
(O)m3 (X1)g4 (O)m3
D1-37
N
N
(X1)g1
D1-38
N
N
(X1)g1
N
N
(X1b)f6 (X1)g3
(X1b)f5
D1-43 D1-44
O
N
(X1b)f4
D1-45
O
N N N
X1a
(X1b)f4
(X1)g3
(X1b)f1
D1-46 D1-47
N
N O
N
O
N
(X1)g3
(X1b)f1
(X1b)f1
(X1b)f4
R12
(X1)g3
D1-48 D1-49 D1-50
S
N
S
N
(X1)g3
(X1b)f1
(X1b)f4
D1-51 D1-52
N
O
(X1b)f6
N
N N
N
(X1)g3
(X1b)f1
(X1b)f4
X1a X1a
D1-53 D1-54 D1-55
O
N N
N
(X1b)f6
X1a (X1)g3
(X1b)f5
D1-56 D1-57
O
N
(X1b)f6
O N
(X1b)f5
(X1)g3
N
N
(X1)g3
(X1b)f5
X1a
D1-58 D1-59 D1-60
S
N
(X1b)f6 N
N
(X1b)f6
N N
(X1b)f5
(X1)g3
X1a
X1a
S N
(X1b)f5
(X1)g3
O
O
N
(X1b)f2
D1-61 D1-62 D1-63 D1-64 D1-65
286
X1 is a halogen atom, cyano, nitro, -OH, -SH or R24, provided that when g1, g2 or g4 is
an integer of at least 2, each X1 may be identical with or different from one another,
and when there are two neighboring X1’s, the two neighboring X1’s may form
-CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH25 -,
-CH2CH2CH2CH2-, -CH2CH2CH2O-, -CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH2O-,
-CH2CH2CH2S- or -OCH2CH2S- to form, together with the carbon atoms attached to
O
N
O O
O N
(X1b)f4
(X1b)f1
(X1)g3
O
S
N
O
N
N
X1a
(X1b)f2 (X1b)f2
N
N
O
(X1b)f4
X1a
O
N
(X1b)f8
D1-66 D1-67 D1-68 D1-69
D1-72
D1-76 D1-78 D1-79
O (X1b)f1
O
(X1b)f5
D1-80
S
(X1b)f5
D1-82
S
(X1b)f 7
(O)r
D1-81
O
(X1b)f7
D1-83
N
(X1b)f7
X1a
D1-84
O
O
(X1b)f5
D1-85
S
O
(X1b)f5
D1-86
N
O
(X1b)f5
X1a
D1-87
S
S
(X1b)f5
D1-88
N
S
(X1b)f 5
X1a
N
O
(X1b)f6
N
S
(X1b)f6
D1-89 D1-90
S
N
O
(X1b)f4
D1-70
O
S N
(X1b)f1
(X1)g3
D1-71
O
N N
(X1b)f1
(X1)g3
D1-73
X1a
O
N
N
N
(X1b)f4 O N
(X1b)f1
(X1)g3
D1-74 D1-75
X1a
O
N
(X1b)f8
D1-77
X1a
D1-92
O
(X1b)f9
D1-93
S
(X1b)f 9
(O)r
D1-94
N
(X1b)f9
X1a
D1-95
O
O
(X1b)f7
D1-96
S
O
(X1b)f7
D1-97
O N
(X1b)f7
X1a
D1-98
S
S
(X1b)f7
D1-99
S N
(X1b)f7
X1a
N
N
(X1b)f6
X1a
D1-91
287
the X1’s, a 5-membered ring or 6-membered ring which may have one or more
hydrogen atoms on the ring-constituting carbon atoms optionally replaced by one or
more halogen atoms, one or more C1-C6 alkyl groups, one or more C1-C6 haloalkyl
groups, one or more C1-C6 alkoxy groups, one or more C1-C6 alkylthio groups, one or
more C1-C6 alkylsulfinyl groups or one or more C1-C6 alkylsulfonyl groups5 ,
X1a is a hydrogen atom, cyano, -OH or R24,
X1b is a halogen atom, cyano, nitro, -OH, -SH or R24, provided that when f1, f2, f4, f5,
f6, f7, f8 or f9 is an integer of at least 2, each X1b may be identical with or different from
one another, and when there are two X1b’s on the same carbon, the two X1b’s may form
10 oxo, thioxo, imino, C1-C6 alkylimino, C1-C6 alkoxyimino or C1-C6 alkylidene together
with each other,
Z is a halogen atom, cyano, nitro, -OH, -SH or R24, provided that q is an integer of at
least 2, each Z may be identical with or different from one another, and when there are
two neighboring Z’s, the two neighboring Z’s may form -CH2CH2CH2-, -CH2CH2O-,
15 -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -CH2CH2CH2CH2-, -CH2CH2CH2O-,
-CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH2O-, -CH2CH2CH2S- or -OCH2CH2S- to form,
together with the carbon atoms attached to the Z’s, a 5-membered ring or a 6-
membered ring which may have one or more hydrogen atoms on the ring-constituting
carbon atoms optionally replaced by one or more halogen atoms, one or more C1-C6
20 alkyl groups, one or more C1-C6 haloalkyl groups, one or more C1-C6 alkoxy groups,
one or more C1-C6 alkylthio groups, one or more C1-C6 alkylsulfinyl groups or one or
more C1-C6 alkylsulfonyl groups,
Z3 is a halogen atom, nitro, -OH, -SH or R24, provided that q is an integer of at least 2,
each Z3 may be identical with or different from one another, and when there are two
25 neighboring Z3’s, the neighboring two Z’s may form -CH2CH2CH2-, -CH2CH2O-,
-CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -CH2CH2CH2CH2-, -CH2CH2CH2O-,
-CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH2O-, -CH2CH2CH2S- or -OCH2CH2S- to form,
together with the carbon atoms attached to the Z3’s, a 5-membered ring or a 6-
membered ring which may have one or more hydrogen atoms on the ring-constituting
30 carbon atoms optionally replaced by one or more halogen atoms, one or more C1-C6
alkyl groups, one or more C1-C6 haloalkyl groups, one or more C1-C6 alkoxy groups,
one or more C1-C6 alkylthio groups, one or more C1-C6 alkylsulfinyl groups or one or
more C1-C6 alkylsulfonyl groups,
R24 is a C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28, C2-C6 alkenyl, (C2-C6)
35 alkenyl optionally substituted with R28, C3-C8 cycloalkenyl, (C3-C8) cycloalkenyl
optionally substituted with R28, C2-C6 alkynyl, (C2-C6) alkynyl optionally substituted with
R28, C3-C8 cycloalkyl, (C3-C8) cycloalkyl optionally substituted with R28, -OR25,
-S(O)rR25, -C(O)OH, -C(O)OR25a, -C(O)R26, -C(O)N(R27a)R27, -C(S)N(R27a)R27,
-N(R27a)R27, -C(=NOR25)R26 or -S(O)2N(R27a)R27,
40 each of R25, R25a and R26 is independently C1-C6 alkyl or (C1-C6) alkyl optionally
substituted with R32a,
each of R27 and R27a is independently a hydrogen atom, C1-C6 alkyl, -S(O)rR34 or
-C(O)R34,
each of R28 and R28a is independently a halogen atom, -OH, -OR29, -SH or -S(O)rR29,
45 each of R29 and R33 is independently C1-C6 alkyl,
each of R32 and R32a is independently a halogen atom, -OR33 or -S(O)rR33,
R34 is C1-C6 alkyl, C3-C8 cycloalkyl or C1-C6 haloalkyl,
288
each of n, g1 and f1 is independently an integer of from 0 to 3,
g2 is an integer of from 0 to 2,
g3 is an integer of from 0 to 1,
each of g4 and f4 is independently an integer of from 0 to 4,
f5 is an integer of from 0 to 55 ,
f6 is an integer of from 0 to 6,
f7 is an integer of from 0 to 7,
f8 is an integer of from 0 to 8,
f9 is an integer of from 0 to 9,
10 q is an integer of from 1 to 5,
q2 is an integer of from 0, 1 or 3 to 5,
each of m1, m2 and m3 is independently an integer of from 0 or 1, and
r is an integer of from 0 to 2.
2. The pyrazole derivative or a salt thereof according to claim 1, wherein Rb is
15 -C(O)R7, -C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(S)OR6a, -C(S)SR6a, -C(O)N(R8a)R8,
-C(S)N(R8a)R8, -C(O)N(R8b)N(R8a)R8, -C(O)N(R8a)OR6a, -C(=NR8b)OR6a,
-C(=NR8b)SR6a, -C(=NR8b)N(R8a)R8, -C(=NR8b)R7, D1-49, D1-51, D1-53, D1-59, D1-61
or D1-63, or Rb may form =C(Rb2)Rb3 together with Ra.
3. The pyrazole derivative or a salt thereof according to claim 2, wherein A1 is -CR1,
20 each of R1 and R3 is independently a hydrogen atom, a halogen atom, cyano, -NH2,
C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28a, C1-C6 alkoxy, C1-C6 alkylthio,
C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 alkoxycarbonyl,
R2 is a halogen atom, C1-C6 alkyl or C1-C6 alkoxy, and
R4 is a hydrogen atom, a halogen atom, cyano, -NH2, C1-C6 alkyl, (C1-C6) alkyl
25 optionally substituted with R28a, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-
C6 alkylsulfonyl.
4. The pyrazole derivative or a salt thereof according to claim 2, wherein A1 is -N(-
O)m2,
R2 is a halogen atom, C1-C6 alkyl or C1-C6 alkoxy, and
30 each of R3 and R4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or
C1-C6 alkoxy.
5. The pyrazole derivative or a salt thereof according to claim 3, wherein R1 is a
hydrogen atom, a halogen atom, cyano, -NH2, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6
alkoxy,
35 R2 is C1-C6 alkyl,
R3 is a hydrogen atom, a halogen atom, cyano, C1-C6 alkyl, (C1-C6) alkyl optionally
substituted with R28a, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl or C1-C6
alkoxycarbonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 alkylthio,
40 Ra is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R5, C2-C6
alkenyl, C2-C6 alkynyl, -S(O)rR6, -C(O)R7a, -C(O)OR6a, -NR8cR8d or -C(=NR8b)R7a,
Rb is -C(O)R7, -C(S)R7, -C(O)OR6a, -C(O)SR6a, -C(O)N(R8a)R8, -C(S)N(R8a)R8,
-C(O)N(R8b)N(R8a)R8, -C(=NR8b)SR6a, -C(=NR8b)N(R8a)R8, -C(=NR8b)R7 or D1-51, or
Rb may form =C(Rb2)Rb3 together with Ra,
45 Rb2 is a hydrogen atom, C1-C6 alkyl or -S(O)rR6,
Rb3 is (C1-C6) alkyl optionally substituted with R14, -OR6 or -N(R8b)R8, or Rb3 may form,
together with Rb2, a C4 alkylene chain to form a 5-membered ring together with the
289
carbon atom attached to Rb3 and Rb2, wherein the alkylene chain may contain a sulfur
atom and a nitrogen atom and may optionally be substituted with -C(O)R7,
R5 is a halogen atom, cyano, C3-C8 cycloalkyl, -OR11, -S(O)rR11, -C(O)OR11a,
-C(=NOR11)R12, -Si(R9a)(R9b)R9, phenyl or D1-37,
R6 is C1-C6 alkyl or (C1-C6) alkyl optionally substituted with 5 th R14,
R6a is C1-C6 alkyl or phenyl substituted with (Z)q,
R7 is C1-C15 alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8 cycloalkyl, (C3-C8)
cycloalkyl optionally substituted with R14, C2-C6 alkenyl, (C2-C6) alkenyl optionally
substituted with R14, C3-C8 cycloalkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally
10 substituted with R14, -C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13, -C(=NOR11)R12, phenyl
substituted with (Z)q, D1-1, D1-2, D1-4, D1-5, D1-6, D1-8, D1-9, D1-10, D1-12, D1-13,
D1-19, D1-32, D1-33, D1-35, D1-38, D1-45, D1-81, D1-82, D1-87, D1-88, D1-92 or
D1-94, or R7 may form, together with Ra, a C2-C4 alkylene chain or a C2-C4 alkenylene
chain containing a double bond to form a 4 to 6-membered ring together with the
15 carbon atom attached to R7 and the nitrogen atom attached to Ra, wherein the alkylene
chain may contain one or two oxygen atoms or nitrogen atoms and may optionally be
substituted with a halogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with
R14, -OR11, -S(O)rR11, an oxo group or a methylidene group,
R7a is a hydrogen atom or C1-C6 alkyl,
20 R8 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8
cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, -C(O)R12, -C(O)OR11a, -C(=NOR11)R12,
-S(O)2R11a, phenyl, phenyl substituted with (Z)q, D1-32, D1-33, D1-34 or D1-80,
R8a is a hydrogen atom, C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R14a, or
R8a may form, together with Ra, a C2-C3 alkylene chain to form a 5 to 6-membered ring
25 together with the nitrogen atom attached to R8a and the nitrogen atom attached to Ra,
wherein the alkylene chain may contain an oxygen atom and may optionally be
substituted with (C1-C6) alkyl optionally substituted with R14 or an oxo group, or R8 and
R8a may form, together with each other, a C5 alkylene chain to form a 6-membered ring
together with the nitrogen atom attached to R8 and R8a, wherein the alkylene chain
30 may optionally be substituted with C1-C6 alkyl, or R8 may form =C(R8f)R8e together with
R8a,
R8b is a hydrogen atom, cyano, C1-C6 alkyl or -OR11,
R8c is a hydrogen atom, C1-C6 alkyl or -C(O)OR11a,
R8d is a hydrogen atom, -C(O)OR11a or -C(O)R12,
35 R8e is a hydrogen atom,
R8f is -N(R13a)R13,
each of R9, R9a, R9b and R10 is independently C1-C6 alkyl,
R11 is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14a or C1-C6 alkenyl,
R11a is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14a or phenyl,
40 R12 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14a, C3-C8
cycloalkyl, -C(=NOR15)R16 or D1-2,
R13 is C1-C6 alkyl or phenyl,
R13a is a hydrogen atom or C1-C6 alkyl,
R14 is a halogen atom, cyano, C3-C8 cycloalkyl, -OH, -OR15, -SH, -S(O)rR15,
45 -S(=NR17b)R15a, -S(O)(=NR17b)R15a, -C(O)OH, -C(O)OR15a, -C(O)N(R17a)R17,
-C(=NOR15)R16, -N(R17a)R17, -ON=C(R16a)R16, -S(O)2N(R17a)R17, -Si(R9a)(R9b)R9,
-P(O)(OR10)2, phenyl, phenyl substituted with (Z)q, D1-1, D1-2, D1-5, D1-7, D1-8, D1-
290
28, D1-32, D1-33, D1-34, D1-84, D1-85, D1-87, D1-93 or D1-98,
R14a is a halogen atom, -OR15, -S(O)rR15, -Si(R9a)(R9b)R9 or phenyl,
R15 is cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C1-C6) alkyl optionally
substituted with R19, -C(O)R21, phenyl substituted with (Z)q2, D1-12, D1-32, D1-37 or
D1-5 51,
R15a is C1-C6 alkyl,
R16 is C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R19,
R16a is a hydrogen atom,
R17 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R19,
10 -S(O)rR20, -C(O)OR20a, -C(O)R21, -C(O)N(R22a)R22, -C(S)N(R22a)R22, -C(=NOR20)R21,
-S(O)2N(R22a)R22 or phenyl,
R17a is a hydrogen atom or C1-C6 alkyl, or R17a may form =C(R17c)R17d together with R17,
R17b is cyano,
R17c is -N(R22a)R22,
15 R17d is a hydrogen atom,
R19 is a halogen atom, cyano, C3-C8 cycloalkyl, -OR20, -S(O)rR20, -C(O)OR20a,
-C(O)N(R22a)R22, -C(=NOR20)R21, -Si(R9a)(R9b)R9, phenyl or D1-34,
R20 is C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R32,
R20a is C1-C6 alkyl,
20 R21 is a hydrogen atom, C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R32,
R22 is C1-C6 alkyl,
R22a is a hydrogen atom or C1-C6 alkyl,
X1 is a halogen atom, cyano, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with
R28, C3-C8 cycloalkyl, -OR25, -S(O)rR25, -C(O)R26, -C(=NOR25)R26 or -S(O)2N(R27a)R27,
25 provided that when g2 is an integer of 2, each X1 may be identical with or different from
each other,
X1a is C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28, -C(O)OR25a or -C(O)R26,
X1b is (C1-C6) alkyl optionally substituted with R28, provided that when f5 is an integer
of 3, each X1b may be identical with or different from one another, and when there are
30 two X1b’s on the same carbon, the two X1b’s may form oxo together with each other,
Z is a halogen atom, nitro, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R28,
-S(O)rR25, -C(O)OH or -C(O)N(R27a)R27, provided that when q is an integer of at least 2,
and there are two neighboring Z’s , the two neighboring Z’s may form -OCH2O- to form,
together with the carbon atoms attached to the Z’s, a 5-membered ring which may
35 have one or more hydrogen atoms on the ring-constituting carbon atoms optionally
replaced by one or more halogen atoms,
each of R25 and R26 is independently C1-C6 alkyl or (C1-C6) alkyl optionally substituted
with R32a,
each of R25a, R29, R33 and R34 is independently C1-C6 alkyl,
40 R27 is a hydrogen atom or -S(O)rR34,
R27a is a hydrogen atom,
each of R28 and R28a is independently a halogen atom, -OH, -OR29 or -S(O)rR29,
R32 is a halogen atom, -OR33 or -S(O)rR33,
R32a is a halogen atom or -S(O)rR33,
45 n is an integer of from 0 to 1,
each of g1 and g2 is independently an integer of from 0 to 2,
each of g3, f7, f9 and m3 is independently an integer of 0,
291
g4 is an integer of from 0 to 1,
f5 is an integer of from 0 to 3,
q is an integer of from 1 to 2,
q2 is an integer of 1, and
r is an integer of from 0 5 to 2.
6. The pyrazole derivative or a salt thereof according to claim 1, wherein R1, R2 and
R4 are hydrogen atoms,
Ra is a hydrogen atom or C1-C6 alkyl,
Rb is -S(O)rR6,
10 R6 is C1-C6 alkyl, C2-C6 alkenyl or (C1-C6) alkyl optionally substituted with R14,
R14 is -S(O)rR15,
R15 is C1-C6 alkyl, and
r is an integer of from 0 to 2.
7. The pyrazole derivative or a salt thereof according to claim 5, wherein R7 is C1-
15 C15 alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8 cycloalkyl, (C3-C8)
cycloalkyl optionally substituted with R14, C2-C6 alkenyl, (C2-C6) alkenyl optionally
substituted with R14, C3-C8 cycloalkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally
substituted with R14, -C(O)OR11a, -C(O)R12, -C(O)N(R13a)R13, -C(=NOR11)R12, phenyl
substituted with (Z)q, D1-1, D1-2, D1-4, D1-5, D1-6, D1-8, D1-9, D1-10, D1-12, D1-13,
20 D1-19, D1-32, D1-33, D1-35, D1-38, D1-45, D1-81, D1-82, D1-87, D1-88, D1-92 or
D1-94,
R8a is a hydrogen atom, C1-C6 alkyl or (C1-C6) alkyl optionally substituted with R14a, or
R8 may form, together with R8a, a C5 alkylene chain to form a 6-membered ring
together with the nitrogen atom attached to R8 and R8a, wherein the alkylene chain
25 may optionally be substituted with C1-C6 alkyl, or R8 and R8a may form =C(R8f)R8e
together with each other.
8. The pyrazole derivative or a salt thereof according to claim 5, wherein R7 may
form, together with Ra, a C2-C4 alkylene chain or a C2-C4 alkenylene chain containing a
double bond to form a 4 to 6-membered ring together with the carbon atom attached to
30 R7and the nitrogen atom attached to Ra, wherein the alkylene chain may contain one
or two oxygen atoms or nitrogen atoms and may optionally be substituted with a
halogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, -OR11,
-S(O)rR11, an oxo group or a methylidene group,
R8 is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with R14, C3-C8
35 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, -C(O)R12, -C(O)OR11a, -C(=NOR11)R12,
-S(O)2R11a, phenyl, phenyl substituted with (Z)q, D1-32, D1-33, D1-34 or D1-80,
R8a may form, together with Ra, a C2-C3 alkylene chain to form a 5 to 6-membered ring
together with the nitrogen atom attached to R8aand the nitrogen atom attached to Ra,
wherein the alkylene chain may contain an oxygen atom and may optionally be
40 substituted with (C1-C6) alkyl optionally substituted with R14or an oxo group,
R14 is a halogen atom or -S(O)rR15, and
R15 is C1-C6 alkyl.
9. The pyrazole derivative or a salt thereof according to claim 4, wherein R4 is a
hydrogen atom,
45 R3 is a halogen atom,
Ra is C1-C6 alkyl,
Rb is -C(O)R7,
R7 is (C-Cs) alkyl optionally substituted with R14,
R14 is -S(0)rR1s,
R15 is Ci-Ce alkyl, and
m2? n and r are integers of 0.
10. A pesticide containing one or more pyrazole derivatives or salts thereof selected
from the pyrazole derivatives and salts thereof as defined in claims 1 to 9, as active
ingredient(s).
11 An agrochemical containing one or more pyrazole derivatives or salts thereof
selected from the pyrazole derivatives and salts thereof as defined in claims 1 to 9, as
active ingredient(s).
12. A parasticide for an internal or external parasite in or on a mammal or bird, which
contains one or more pyrazole derivatives or salts thereof selected from the pyrazole
derivatives and salts thereof as defined in claims 1 to 9, as active ingredients:.
13. An insecticide or miticide containing one or more pyrazole derivatives or salts
thereof selected from the pyrazole derivatives and salts thereof as defined in claims 1
to 9, as active ingredient(s).
14. A seed treatment agent containing one or more pyrazole derivatives or salts
thereof selected from the pyrazole derivatives and salts thereof as defined in claims 1
to 9, as active ingredient(s).
15. The seed treatment agent according to claim 14, which is used to treat seeds by
dipping.
16. A soil treatment agent containing one or more pyrazole derivatives or salts
thereof selected from the pyrazole derivatives and salts thereof as defined in claims 1
to 9, as active ingredient(s).
17. The soil treatment agent according to claim 16, which is used to treat soil by
irrigation.