Technical Field
The present disclosure relates to a novel triazolopyridine
compound or a salt thereof.
Background Art
10 In recent years, the use of insecticides has resulted in
several serious problems, chief among them environmental
contamination and the development of resistance in pest species.
Because insecticides are poisonous compounds, they may adversely
affect non-target organisms besides harmful insects. The
15 accumulation of some insecticides in the environment can in fact
pose a serious threat to both wildlife and humans.
The development of resistance to insecticides in insect pests
is an important and increasing problem. The adverse effects of
insecticide resistance include crop losses, increased production
20 costs, increased environmental hazards, and socio-economic
problems. Therefore, it is urgent to develop novel insecticides
which are thought to have different actions from commercially
available insecticides.
25 Summary of the Invention
Solution to Problem
The present disclosure provides a triazolopyridine compound
or a salt thereof which has an excellent effect on pests.
The present disclosure also provides a triazolopyridine
30 compound or a salt thereof which has an excellent controlling
effect against pests even when used at a low concentration.
Specifically, as a result of extensive research, the present
inventors have found that a compound represented by the following
general formula (I) or a salt thereof exhibits excellent activity
35 against pests like aphid and whitefly at low concentration.
Thus, the present disclosure relates to a
triazolopyridine compound represented by formula (I) or
thereof shown elsewhere herein.
1
novel
a salt
5
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More specifically, the present disclosure includes the
following embodiments:
Embodiment 1:
A triazolopyridine compound represented by formula (I) Rs
or a salt thereof,
wherein,
RYyR6
z~R7
R1~:8
-~ R2 N
R3 (I)
R1 represents hydrogen, halogen, C1-C5 alkyl, or C3-Cs cycloalkyl,
10 wherein the C1-C6 alkyl, or CrCs cycloalkyl is optionally
substituted with one to five substituents, and each substituent
is independently selected from halogen, hydroxy, cl-c6 alkyl, clc6
haloalkyl' cl-c6 alkoxy' cl-c6 haloalkoxy' cl-c6 alkylcarbonyloxy'
cl-c6 alkoxycarbonyloxy, cl-c6 alkylthio, cl-c6 haloalkylthio, cl-
15 C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or
cl-c6 haloalkylsulfonyl;
R2 represents hydrogen, halogen, hydroxy, formyl, C1-C5 alkyl, C3-
Cs cycloalkyl, CrC6 alkenyl, CrC6 alkynyl, C1-C6 alkoxy, C1-C6
alkylcarbonyloxy, CrCs cycloalkylcarbonyloxy, C1-C6
20 alkoxycarbonyloxy, cl-c6 alkylthio, cl-c6 alkylsulfinyl, cl-c6
alkylsulfonyl, C1-C5 alkoxycarbonyl, CONR9R10 , C02H, NR9R10 , aryl,
or heteroaryl, wherein the C1-C6 alkyl, C3-C8 cycloalkyl, C2-C6
alkenyl, C2-C6 alkynyl, Cl-C6 alkoxy, Cl-C6 alkylcarbonyloxy, C3-Cs
cycloalkylcarbonyloxy' cl-c6 alkoxycarbonyloxy' cl-c6 alkyl thio'
25 CcC6 alkylsul finyl, CcC6 alkylsul fonyl, Cl-C6 alkoxycarbonyl,
aryl, or heteroaryl is optionally substituted with one to five
substituents, and each substituent is independently selected from
halogen, hydroxy, cl-c6 alkyl, cl-c6 haloalkyl, cl-c6 alkoxy, cl-c6
haloalkoxy, cl-c6 alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6
30 alkyl thio, C1-c6 haloalkyl thio, C1-c6 alkylsulfinyl, C1-c6
haloalkylsulfinyl,
haloalkylsulfonyl;
2
alkyl sulfonyl, or
wo 2022/003510 PCT/IB2021/055648
R3 represents hydrogen, halogen, C1-C5 alkyl, C3-Cs cycloalkyl, or
C1-c6 alkoxy, wherein the C1-c6 alkyl, CrCs cycloalkyl, or C1-c6
alkoxy is optionally substituted with one to five substituents,
and each substituent is independently selected from halogen,
5 hydroxy, cl-c6 alkyl, cl-c6 haloalkyl, cl-c6 alkoxy, cl-c6
haloalkoxy, cl-c6 alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6
alkyl thio, C1-c6 haloalkyl thio, C1-c6 alkylsulfinyl, C1-c6
haloalkylsulfinyl,
haloalkylsulfonyl;
alkyl sulfonyl, or
10 R4, R5, R7, and R8 independently represent hydrogen, halogen, ClC6
alkyl, CrCs cycloalkyl, C1-c6 alkoxy, C1-c6 alkyl thio, C1-c6
alkylsul finyl, or C1-c6 alkylsul fonyl, wherein the C1-c6 alkyl, Cr
Cs cycloalkyl, C1-c6 alkoxy, C1-c6 alkylthio, C1-c6 alkylsulfinyl,
or C1-c6 alkylsulfonyl is optionally substituted with one to five
15 substituents, and each substituent is independently selected from
halogen, cl-c6 alkyl' cl-c6 haloalkyl' cl-c6 alkoxy' cl -c6
haloalkoxy, cl-c6 alkylcarbonyloxy, or cl-c6 alkoxycarbonyloxy;
R6 represents hydrogen, halogen, C1-C6 alkyl, C3-Cs cycloalkyl, ClC6
alkoxy, C1-c6 alkylthio, C1-c6 alkylsulfinyl, C1-c6 alkylsulfonyl,
20 aryl, or heteroaryl, wherein the C1-C6 alkyl, CrCs cycloalkyl, ClC6
alkoxy, C1-c6 alkylthio, C1-c6 alkylsulfinyl, C1-c6 alkylsulfonyl,
aryl, or heteroaryl is optionally substituted with one to five
substituents, and each substituent is independently selected from
halogen, hydroxy, cl-c6 alkyl, cl-c6 haloalkyl, cl-c6 alkoxy, cl-c6
25 haloalkoxy, cl-c6 alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6
alkyl thio, CcC6 haloalkyl thio, CcC6 alkylsulfinyl, C1-C6
haloalkylsul finyl, C1-c6 alkyl sulfonyl, or C1-c6
haloalkylsulfonyl;
Z represents an oxygen atom, a sulfur atom, SO, or S02 ;
30 R9 represents hydrogen, Cl-C6 alkyl, C3-Cs cycloalkyl, Cl-C6
alkylcarbonyl, or cl-c6 alkoxycarbonyl, wherein the cl-c6 alkyl,
c3-Cs cycloalkyl, C1-c6 alkylcarbonyl, or C1-c6 alkoxycarbonyl is
optionally substituted with one to five substi tuents, and each
substituent is independently selected from halogen, hydroxy, cl-
35 c6 alkyl, cl-c6 haloalkyl, cl-c6 alkoxy, cl-c6 haloalkoxy, cl-c6
alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6 alkylthio, cl-c6
haloalkylthio, cl-c6 alkylsulfinyl, cl-c6 haloalkylsulfinyl, cl-c6
alkylsulfonyl, or C1-C6 haloalkylsulfonyl;
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R10 represents hydrogen, Cl-C6 alkyl, or C3-Cs cycloalkyl, wherein
the C1-c6 alkyl, or C3-Cs cycloalkyl is optionally substituted with
one to five substituents, and each substituent is independently
selected from halogen, hydroxy, cl-c6 alkyl, cl-c6 haloalkyl, cl-
5 c6 alkoxy' cl-c6 haloalkoxy' cl-c6 alkylcarbonyloxy' cl-c6
alkoxycarbonyloxy, cl-c6 alkylthio, cl-c6 haloalkylthio, cl-c6
alkylsul finyl, C1-C6 haloalkylsul finyl, C1-C6 alkyl sulfonyl, or C1-
C6 haloalkylsulfonyl; and
provided that the following compounds (i), (ii) and (iii) are
10 excluded,
15
20
25
(i) the compounds wherein Rl is hydrogen, R2 is methyl, R3 is
hydrogen, R4 is hydrogen, Rs is hydrogen, R6 is bromo, R7 is
hydrogen, and RB is hydrogen.
(ii) the compounds wherein Rl is hydrogen, R2 is methyl, R3 is
hydrogen, R4 is hydrogen, R5 is chloro, R6 is chloro, R7 is hydrogen,
and R8 is hydrogen.
(iii) the compounds wherein Rl is hydrogen, R2 is methyl, R3 is
hydrogen, R4 is hydrogen, Rs is hydrogen, R6 is methyl, R7 is
hydrogen, Rs is hydrogen, and z is a sulfur atom.
Embodiment 2:
The triazolopyridine compound or a salt thereof according to
any one of the preceding embodiments, wherein R1 and R3 represent
hydrogen.
Embodiment 3-1:
The triazolopyridine compound or a salt thereof according to any
one of the preceding embodiments, wherein R2 represents hydrogen,
halogen, hydroxy, Cl-C6 alkyl, C3-Cs cycloalkyl, CcC6 alkoxy, C2-C6
30 alkenyl, CcC6 alkoxy-CcC6 alkyl, formyl, carboxy, C1-C6 haloalkyl,
cl-c6 haloalkoxy' cl-c6 alkylcarbonyloxy' cl-c6 alkoxycarbonyl' clc6
alkoxycarbonyloxy, C3-C8 cycloalkylcarbonyloxy, halogensubstituted
aryl, or C1-c6 alkyl-substituted aryl, C1-c6
alkoxycarbonyloxy-Cl-c6 alkyl, C1-c6 alkylcarbonyloxy-Cl-c6 alkyl,
35 hydroxy-substituted c1-c6 alkyl, c1-c6 alkyloxy-Cl-c6 alkyl, c1-c6
alkyl thio, C1-C6 alkylsulfinyl, C1-C6 alkyl sulfonyl, or NR9R10 ,
wherein R9 and R10 each independently represents hydrogen, C1-C6
alkyl, or C1-c6 alkoxycarbonyl.
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Embodiment 3-2:
The triazolopyridine compound or a salt thereof according to
any one of the preceding embodiments, wherein R2 represents
hydrogen, halogen, CcC6 alkyl, C3-Cs cycloalkyl, Cl-C6 alkoxy, C2-
5 C6 alkenyl, C1-C6 alkoxy-Cl-C6 alkyl, formyl, C1-C6 alkylthio, C1-C6
alkylsul finyl, C1-c6 alkylsul fonyl, or NR9R10 , wherein R9 and R10
each independently represents hydrogen or C1-C6 alkyl, and are not
both hydrogen.
10
15
20
25
Embodiment 3-3:
The triazolopyridine compound or a salt thereof according to
any one of the preceding embodiments, wherein R2 represents C1-C6
alkyl, CrCs cycloal kyl, C1-c6 alkoxy, C1-c6 alkyl thio.
Embodiment 4-1:
The triazolopyridine compound or a salt thereof according to
any one of the preceding embodiments, wherein R4 , R5 , R7 , and R8
each independently represents hyderogen, halogen, C1-C6 alkyl, C1-
C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C6 haloalkyl thio.
Embodiment 4-2:
The triazolopyridine compound or a salt thereof according to
any one of the preceding embodiments, wherein R4 , R5 , R7 , and R8
each independently represents hydrogen, halogen, C1-c6 haloalkyl,
or cl-c6 haloalkoxy.
Embodiment 4-3:
The triazolopyridine compound or a salt thereof according to
any one of the preceding embodiments, wherein R4 , R5 , R7 , and R8
independently represent hydrogen, halogen, or cl-c6 haloalkoxy.
Embodiment 4-4:
The triazolopyridine compound or a salt thereof according to
30 any one of the preceding embodiments, wherein R4 represents
hydrogen or halogen.
Embodiment 4-5:
The triazolopyridine compound or a salt thereof according to
any one of the preceding embodiments, wherein R5 represents
35 hydrogen, halogen, cl-c6 haloalkyl, or cl-c6 haloalkoxy.
Embodiment 4-6:

[Claim 1]
A triazolopyridine compound represented by formula (I)
Rs
5 or a salt thereof,
wherein,
R\)yRs
z~R7 R1¢:8
~~
R2 N
R3 (I)
R1 represents hydrogen, halogen, C1-C6 alkyl, or C3-C8 cycloalkyl,
wherein the C1-c6 alkyl, or C3-Cs cycloalkyl is optionally
substituted with one to five substituents, and each substituent
10 is independently selected from halogen, hydroxy, cl-c6 alkyl, clc6
haloalkyl' cl-c6 alkoxy' cl-c6 haloalkoxy' cl-c6 alkylcarbonyloxy'
cl-c6 alkoxycarbonyloxy, cl-c6 alkylthio, cl-c6 haloalkylthio, clc6
alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, or
cl-c6 haloalkylsulfonyl;
15 R2 represents hydrogen, halogen, hydroxy, formyl, C1-C6 alkyl, C3-
Cs cycloalkyl, CrC6 alkenyl, CrC6 alkynyl, C1-C6 alkoxy, C1-C6
alkylcarbonyloxy, CrCs cycloalkylcarbonyloxy, C1-C6
alkoxycarbonyloxy, cl-c6 alkylthio, cl-c6 alkylsulfinyl, cl-c6
alkylsul fonyl, C1-C6 alkoxycarbonyl, CONR9R10 , C02H, NR9R10 , aryl,
2 0 or heteroaryl, wherein the Cl-C6 alkyl, C3-Cs cycloalkyl, C2-C6
alkenyl, C2-c6 alkynyl, C1-c6 alkoxy, C1-c6 alkylcarbonyloxy, C3-Cs
cycloalkylcarbonyloxy' cl-c6 alkoxycarbonyloxy' cl-c6 alkyl thio'
CcC6 alkylsul finyl, CcC6 alkylsul fonyl, C1-C6 alkoxycarbonyl,
aryl, or heteroaryl is optionally substituted with one to five
25 substituents, and each substituent is independently selected from
halogen, hydroxy, cl-c6 alkyl, cl-c6 haloalkyl, cl-c6 alkoxy, cl-c6
haloalkoxy, cl-c6 alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6
alkyl thio, C1-c6 haloalkyl thio, C1-c6 alkylsulfinyl, C1-c6
haloalkylsulfinyl,
30 haloalkylsulfonyl;
alkyl sulfonyl, or
R3 represents hydrogen, halogen, C1-C6 alkyl, C3-C8 cycloalkyl, or
95
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alkoxy is optionally substituted with one to five substituents,
and each substituent is independently selected from halogen,
hydroxy, CcC6 alkyl, C1-C6 haloalkyl, CcC6 alkoxy, C1 -C6
haloalkoxy, cl-c6 alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6
5 alkyl thio, C1-c6 haloalkyl thio, C1-c6 alkylsulfinyl, C1-c6
haloalkylsul finyl, C1-c6 alkyl sulfonyl, or C1-c6
haloalkylsulfonyl;
R4 , R5 , R7 , and R8 independently represent hydrogen, halogen, ClC6
alkyl, CrCs cycloalkyl, C1-C6 alkoxy, C1-C6 alkyl thio, C1-C6
10 alkylsulfinyl, or C1-c6 alkylsulfonyl, wherein the C1-c6 alkyl, Cr
Cs cycloalkyl, C1-c6 alkoxy, C1-c6 alkylthio, C1-c6 alkylsulfinyl,
or C1-C6 alkylsulfonyl is optionally substituted with one to five
substituents, and each substituent is independently selected from
halogen, cl-c6 alkyl' cl-c6 haloalkyl' cl-c6 alkoxy' cl -c6
15 haloalkoxy, cl-c6 alkylcarbonyloxy, or cl-c6 alkoxycarbonyloxy;
R6 represents hydrogen, halogen, C1-C6 alkyl, C3-Cs cycloalkyl, ClC6
alkoxy, C1-c6 alkylthio, C1-c6 alkylsulfinyl, C1-c6 alkylsulfonyl,
aryl, or heteroaryl, wherein the C1-C6 alkyl, C3-Cs cycloalkyl, ClC6
alkoxy, C1-c6 alkylthio, C1-c6 alkylsulfinyl, C1-c6 alkylsulfonyl,
2 0 aryl, or heteroaryl is optionally substituted with one to five
substituents, and each substituent is independently selected from
halogen, hydroxy, cl-c6 alkyl, cl-c6 haloalkyl, cl-c6 alkoxy, cl-c6
haloalkoxy, cl-c6 alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6
alkyl thio, C1-c6 haloalkyl thio, C1-c6 alkylsulfinyl, C1-c6
25 haloalkylsulfinyl,
haloalkylsulfonyl;
alkyl sulfonyl, or
Z represents an oxygen atom, a sulfur atom, SO, or S02 ;
R9 represents hydrogen, C1-C5 alkyl, C3-Cs cycloalkyl, C1-C5
alkylcarbonyl, or C1-C6 alkoxycarbonyl, wherein the C1-C6 alkyl,
30 C3-C8 cycloalkyl, CcC6 alkyl carbonyl, or CcC6 alkoxycarbonyl is
optionally substituted with one to five substi tuents, and each
substituent is independently selected from halogen, hydroxy, C1 -
C6 alkyl, C1 -C6 haloal kyl, C1-C6 al koxy, C1-C6 haloal koxy, C1 -C6
alkylcarbonyloxy, cl-c6 alkoxycarbonyloxy, cl-c6 alkylthio, cl-c6
35 haloalkylthio, cl-c6 alkylsulfinyl, cl-c6 haloalkylsulfinyl, cl-c6
alkylsulfonyl, or C1-C6 haloalkylsulfonyl;
R10 represents hydrogen, C1-C6 alkyl, or C3-C8 cycloalkyl, wherein
the C1-c6 alkyl, or C3-Cs cycloalkyl is optionally substituted with
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one to five substituents, and each substituent is independently
selected from halogen, hydroxy, cl-c6 alkyl, cl-c6 haloalkyl, clalkoxy,
haloalkoxy' cl-c6 alkylcarbonyloxy'
alkoxycarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio,
5 alkylsul finyl, C1-C6 haloalkylsul finyl, C1-C6 alkyl sulfonyl, or C1-
C6 haloalkylsulfonyl; and
10
provided that the following compounds (i), (ii) and (iii) are
excluded,
( i) the compounds wherein R1 is hydrogen,
hydrogen, R4 is hydrogen, R5 is hydrogen,
hydrogen, and R8 is hydrogen.
R2 is methyl,
R6 is bromo,
is
is
(ii) the compounds wherein R1 is hydrogen, R2 is methyl, R3 is
hydrogen, R4 is hydrogen, R5 is chloro, R6 is chloro, R7 is hydrogen,
and R8 is hydrogen.
15 (iii) the compounds wherein R1 is hydrogen, R2 is methyl, R3 is
hydrogen, R4 is hydrogen, R5 is hydrogen, R6 is methyl, R7 is
hydrogen, R8 is hydrogen, and Z is a sulfur atom.
[Claim 2]
20 The triazolopyridine compound or a salt thereof according to any
one of the preceding claims, wherein R1 and R3 represents hydrogen.
[Claim 3]
The triazolopyridine compound or a salt thereof according to any
25 one of the preceding claims, wherein R2 represents C1-C6 alkyl,
CrCs cycloalkyl, Cl-c6 alkoxy, or Cl-c6 alkyl thio.
[Claim 4]
The triazolopyridine compound or a salt thereof according to any
30 one of the preceding claims, wherein R4 , R5 , R7 , and R8
independently represent hydrogen, halogen, or cl-c6 haloalkoxy.
[Claim 5]
The triazolopyridine compound or a salt thereof according to any
35 one of the preceding claims, wherein R6 represents C1-c6 haloalkoxy,
or C1-c6 haloalkylthio.
[Claim 6]
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A pest controlling agent comprising the triazolopyridine compound
or a salt thereof according to any one of the claims 1 to 5 as an
active ingredient.
5 [Claim 7]
A method for using the triazolopyridine compound or a salt thereof
according to any one of the claims 1 to 5 for controlling pests.
[Claim 8]
10 A method for controlling pests, which comprises applying the
triazolopyridine compound or a salt thereof according to any one
of the claims 1 to 5 to a plant or its vicinity, or soil where a
plant is cultivated.
15 [Claim 9]
20
25
30
A method for controlling pests, which comprises applying an
effective amount of the triazolopyridine compound or a salt
thereof according to any one of the claims 1 to 5 to pests, a
habitat of a pest, or a place where inhabitation is predicted.
[Claim 10]
A composition for controlling pests, comprising the
triazolopyridine compound or a salt thereof according to any one
of the claims 1 to 5 as an active ingredient.
[Claim 11]
Use of the triazolopyridine compound or a salt thereof according
to any one of the claims 1 to 5 for controlling pests.