DESCRIPTION
TITLE OF INVENTION:
CONDENSED HETEROCYCLIC COMPOUNDS AND PESTICIDES
5 TECHNICAL FIELD
The present invention relates to a novel condensed heterocyclic compound and its
salt, and a pesticide containing the compound as an active ingredient.
BACKGROUND ART
10 For example, Patent Documents 1 to 31 disclose condensed heterocyclic
compounds, however, they failed to disclose the condensed heterocyclic compounds of
the present invention. Usefulness of the compounds as pesticides, especially, as
insecticides, acaricides or parasiticides against internal or external parasites in or on a
mammal or bird is not known at all.
15
PRIOR ART DOCUMENTS
PATENT DOCUMENTS
Patent Document 1: WO2016/005263
Patent Document 2: WO2015/198859
20 Patent Document 3: WO2015/133603
Patent Document 4: WO2015/121136
Patent Document 5: WO2015/091945
Patent Document 6: WO2015/087458
Patent Document 7: WO2015/071180
25 Patent Document 8: WO2015/059088
Patent Document 9: WO2015/002211
Patent Document 10: WO2015/000715
Patent Document 11: WO2014/157600
Patent Document 12: WO2014/148451
30 Patent Document 13: WO2014/142292
Patent Document 14: WO2014/132972
Patent Document 15: WO2014/132971
2
Patent Document 16: WO2014/123206
Patent Document 17: WO2014/123205
Patent Document 18: WO2014/104407
Patent Document 19: WO2013/180194
Patent Document 5 20: WO2013/180193
Patent Document 21: WO2013/191113
Patent Document 22: WO2013/191189
Patent Document 23: WO2013/191112
Patent Document 24: WO2013/191188
10 Patent Document 25: WO2013/018928
Patent Document 26: WO2012/086848
Patent Document 27: WO2012/074135
Patent Document 28: WO2011/162364
Patent Document 29: WO2011/043404
15 Patent Document 30: WO2010/125985
Patent Document 31: WO2009/131237
DISCLOSURE OF INVENTION
TECHNICAL PROBLEM
20 With the advance of development of pesticides targeted at various pest insects
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
25 resistance to them over many years of their use. Problems of the high toxicity of some
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.
30 It is an object of the present invention to provide a novel pesticide which has
excellent pesticidal activities, which has low toxicity, for example, which has little
harmful effect on non-target organisms such as mammals, fishes and useful insects,
3
and which has low persistence.
SOLUTION TO PROBLEMS
The present inventors have conducted extensive studies to achieve the above
object and as a result, found that a novel condensed 5 heterocyclic compound
represented by the following formula (1) of the present invention is a very useful
compound which has excellent pesticidal activities particularly insecticidal and acaricidal
activities, and which has little harmful effect on non-target organisms such as mammals,
fishes and useful insects, and accomplished the present invention.
10 That is, the present invention relates to the following [1] to [167].
[1] A condensed heterocyclic compound represented by the formula (1) or its salt or
an N-oxide thereof:
wherein D substituted with -S(O)nR1 is a ring represented by any one of D1, D2 and D3:
15
Q is a ring represented by any one of Q1, Q2, Q3 and Q4:
G1 is a nitrogen atom or C(Y1),
G2 is a nitrogen atom or C(Y2),
4
G3 is a nitrogen atom or C(Y3),
G4 is a nitrogen atom or C(Y4),
G5 is a nitrogen atom or C(Y5),
T1 is N(T1a), an oxygen atom or a sulfur atom,
A1 is N(A1a), an oxygen atom 5 or a sulfur atom,
A2 is a nitrogen atom or C(R2),
A3 is a nitrogen atom or C(R3),
A4 is a nitrogen atom or C(R4),
A5 is a nitrogen atom or C(R5),
10 A8 is a nitrogen atom or C(R8),
R1 is C1-C6 alkyl, C1-C6 haloalkyl, (C1-C6) alkyl optionally substituted with R1a, C2-
C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6
halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl, C3-C6 halocycloalkyl (C1-C6) alkyl or
hydroxy (C1-C6) alkyl,
15 R1a is C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl or cyano,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkylthio, C1-C6
20 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, -C(O)R20a, -C(O)OH, hydroxy, -NH2, -NHR20g, -N(R20h)R20g, mercapto,
cyano or nitro,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6
haloalkenyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6
25 halocycloalkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-
C6 haloalkylsulfonyl, -C(O)R30a, -C(O)OH, hydroxy, -OC(O)R30e, -OS(O)2R30f, -NH2, -
NHR30g, -N(R30h)R30g, mercapto, -SC(O)R30i, -SF5, cyano, nitro, phenyl, phenyl
optionally substituted with R3b, heterocyclyl or heterocyclyl optionally substituted with
30 R3b,
R3a is C1-C8 alkoxycarbonyl,
R3b is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy,
5
cyano or nitro,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6
haloalkenyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6
halocycloalkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-5 C6 alkylsulfonyl, C1-
C6 haloalkylsulfonyl, -C(O)R40a, -C(O)OH, hydroxy, -OC(O)R40e, -OS(O)2R40f, -NH2, -
NHR40g, -N(R40h)R40g, mercapto, -SC(O)R40i, -SF5, cyano, nitro, phenyl, phenyl
optionally substituted with R4b, heterocyclyl or heterocyclyl optionally substituted with
R4b,
10 R4a is C1-C8 alkoxycarbonyl,
R4b is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy,
cyano or nitro,
R5 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkylthio, C1-C6
15 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, -C(O)R50a, -C(O)OH, hydroxy, -NH2, -NHR50g, -N(R50h)R50g, mercapto,
cyano or nitro,
R6 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkylthio, C1-C6
20 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, -C(O)R60a, -C(O)OH, hydroxy, -NH2, -NHR60g, -N(R60h)R60g, mercapto,
cyano or nitro,
R7 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
25 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, mercapto, -SF5, cyano or
nitro,
R8 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy or cyano,
A1a is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, (C1-C6) alkyl optionally
30 substituted with A1a-a, (C1-C6) haloalkyl optionally substituted with A1a-a, C2-C6 alkenyl,
C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-
C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl, C3-C6 halocycloalkyl
6
(C1-C6) alkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C(O)R10a, hydroxy or
cyano,
A1a-a is C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C8
haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-5 C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, hydroxy or cyano,
T1a is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6
haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6
10 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl
(C1-C6) alkyl,
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-
C6 alkyl, C1-C6 haloalkyl, (C1-C6) alkyl optionally substituted with Ya, (C1-C6) haloalkyl
optionally substituted with Ya, C2-C6 alkenyl, C2-C6 haloalkenyl, (C2-C6) alkenyl
15 optionally substituted with Ya, C2-C6 alkynyl, C2-C6 haloalkynyl, (C2-C6) alkynyl optionally
substituted with Yb, C1-C8 alkoxy, C1-C8 haloalkoxy, (C1-C8) alkoxy optionally substituted
with Ya, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, (C2-C6) alkenyloxy optionally
substituted with Ya, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy, (C2-C6) alkynyloxy
optionally substituted with Ya, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl
20 (C1-C6) alkyl, C3-C6 halocycloalkyl (C1-C6) alkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with Ya, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-
C6 alkynylthio, C2-C6 haloalkynylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, (C1-C6)
alkylsulfinyl optionally substituted with Ya, C2-C6 alkenylsulfinyl, C2-C6 haloalkenylsulfinyl,
C2-C6 alkynylsulfinyl, C2-C6 haloalkynylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
25 haloalkylsulfonyl, (C1-C6) alkylsulfonyl optionally substituted with Ya, C2-C6
alkenylsulfonyl, C2-C6 haloalkenylsulfonyl, C2-C6 alkynylsulfonyl, C2-C6
haloalkynylsulfonyl, -C(O)R90a, -C(O)NHR90b, -C(O)N(R90c)R90b, -C(O)OH, -
C(=NOR90d)R90a, -C(O)NH2, hydroxy, -OC(O)R90e, -OS(O)2R90f, -NH2, -NHR90g, -
N(R90h)R90g, mercapto, -SC(O)R90i, -S(O)2NHR90j, -S(O)2N(R90k)R90j, -SF5, cyano, nitro,
30 phenyl, phenyl optionally substituted with Yc, heterocyclyl or heterocyclyl optionally
substituted with Yc,
each of Y5 and Y6 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl,
7
C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-
C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl,
mercapto, -SF5, cyano or nitro,
Ya is C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C8
haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-5 C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, hydroxy or cyano,
Yb is C1-C6 alkyl, C3-C6 cycloalkyl, trimethylsilyl or phenyl,
Yc is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy,
10 cyano or nitro,
each of R10a, R20a, R30a, R30e, R40a, R40e, R50a, R60a and R90a is independently a
hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy or C1-C8 haloalkoxy,
each of R20g, R20h, R30f, R30g, R30h, R30i, R40f, R40g, R40h, R40i, R50g, R50h, R60g, R60h,
R90b, R90c, R90i, R90j and R90k is independently C1-C6 alkyl or C1-C6 haloalkyl,
15 R90d is a hydrogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R90e is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8
haloalkoxy, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1-C6) alkylamino or di(C1-C6)
haloalkylamino,
R90f is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1-
20 C6) alkylamino or di(C1-C6) haloalkylamino,
each of R90g and R90h is independently C1-C6 alkyl, C1-C6 haloalkyl, C1-C6
alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 haloalkoxycarbonyl,
C1-C6 alkylaminocarbonyl, C1-C6 haloalkylaminocarbonyl, C1-C6 alkylaminothiocarbonyl,
C1-C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6
25 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl or di(C1-C6) alkylaminosulfonyl, and
n is an integer of 0, 1 or 2.
[2] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], wherein
D substituted with -S(O)nR1 is a ring represented by D1,
30 G1 is C(Y1),
G2 is C(Y2),
G3 is C(Y3),
8
G4 is C(Y4),
A2 is C(R2),
A3 is C(R3),
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl,
C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl 5 (C1-C6) alkyl,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
10 C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
C6 haloalkylsulfonyl,
15 each of R5, R6 and R8 is independently a hydrogen atom, a halogen atom, C1-C6
alkyl or C1-C6 haloalkyl,
R7 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl,
A1a is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A1a-a,
C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R10a,
20 A1a-a is C1-C8 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or
cyano,
R10a is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy,
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-
C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally
25 substituted with Yb, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio,
(C1-C6) alkylthio optionally substituted with Ya, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl,
C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -C(O)R90a, -C(O)NHR90b, -C(O)N(R90c)R90b,
-C(O)OH, hydroxy, -OC(O)R90e, -OS(O)2R90f, -NH2, -NHR90g, -N(R90h)R90g, mercapto, -
SC(O)R90i, -S(O)2NHR90j, -S(O)2N(R90k)R90j, -SF5, cyano, nitro, phenyl, phenyl optionally
30 substituted with Yc, heterocyclyl or heterocyclyl optionally substituted with Yc, and
Ya is C1-C8 alkoxycarbonyl.
[3] The condensed heterocyclic compound or its salt or an N-oxide thereof according
9
to the above [1], wherein
D substituted with -S(O)nR1 is a ring represented by D2,
Q is a ring represented by Q1,
A1 is N(A1a),
5 A2 is C(R2),
A3 is C(R3),
A4 is C(R4),
A5 is a nitrogen atom,
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl,
10 C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
15 C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
C6 haloalkylsulfonyl,
20 A1a is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A1a-a,
C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R10a,
A1a-a is C1-C8 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or
cyano,
R10a is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy,
25 Y5 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, and
Y6 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl.
[4] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], wherein
D substituted with -S(O)nR1 is a ring represented by D3,
30 Q is a ring represented by Q1,
G1 is C(Y1),
G2 is C(Y2),
10
G3 is C(Y3),
G4 is C(Y4),
T1 is N(T1 a ) or a sulfur atom,
A1 is N(A1 a )
5 A2 is C(R2),
A3 is C(R3),
A4 is C(R4),
A5 is a nitrogen atom,
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl,
10 C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
15 C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
C6 haloalkylsulfonyl,
20 A1a is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A1a-a,
C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R10a,
A1a-a is C1-C8 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or
cyano,
R10a is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy,
25 T1 a is a hydrogen atom or C1-C6 alkyl, and
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-
C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, cyano or nitro.
30 [5] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [2], wherein
Q is a ring represented by Q1,
11
A1 is N(A1 a ),
R1 is C1-C6 alkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R3a, C1-C6 haloalkylsulfinyl or C1-C6
5 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R4a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl, and
A1 a is a hydrogen atom or C1-C6 alkyl.
10 [6] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [5], wherein
A4 is C(R4), and
A5 is a nitrogen atom.
[7] The condensed heterocyclic compound or its salt or an N-oxide thereof according
15 to the above [5] or [6], wherein
A4 is C(R4),
A5 is a nitrogen atom,
R2 is a hydrogen atom,
R4 is a hydrogen atom or C1-C6 haloalkyl,
20 Y1 is a hydrogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
Y2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6
alkenyl, (C2-C6) alkynyl optionally substituted with Yb, C1-C8 alkoxy, C1-C6 alkylthio, C1-
C6 haloalkylthio, (C1-C6) alkylthio optionally substituted with Ya, C1-C6 alkylsulfinyl, C1-C6
alkylsulfonyl, -NH2, -NHR90g, nitro, phenyl, phenyl optionally substituted with Yc,
25 thiophen-2-yl, pyridin-3-yl or pyridin-4-yl,
Y3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C6 alkylthio, (C1-C6) alkylthio optionally substituted with Ya, C1-C6 alkylsulfinyl, C1-C6
alkylsulfonyl, -C(O)R90a, -C(O)N(R90c)R90b, -C(O)OH, cyano or nitro,
Y4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
30 C1-C6 alkylthio, C1-C6 alkylsulfonyl, -N(R90h)R90g or cyano,
Ya is C1-C8 alkoxycarbonyl,
Yb is C3-C6 cycloalkyl or trimethylsilyl,
12
Yc is a halogen atom or C1-C6 haloalkyl,
R90a is C1-C8 alkoxy,
each of R90b and R90c is independently C1-C6 alkyl,
R90g is C1-C6 alkyl, C1-C6 haloalkylcarbonyl, C1-C8 alkoxycarbonyl or
phenylcarbonyl, 5 and
R90h is C1-C6 alkyl.
[8] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [5], wherein
A4 is a nitrogen atom, and
10 A5 is C(R5).
[9] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [5] or [8], wherein
A4 is a nitrogen atom,
A5 is C(R5),
15 R2 is a hydrogen atom,
R3 is C1-C6 haloalkyl,
R5 is a hydrogen atom or C1-C6 alkyl,
Y1 is a hydrogen atom,
Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl,
20 Y3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl or cyano, and
Y4 is a hydrogen atom, a halogen atom or C1-C8 alkoxy.
[10] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [2], wherein
Q is a ring represented by Q2,
25 A4 is a nitrogen atom or C(R4),
A5 is a nitrogen atom or C(R5),
(excluding a case where both A4 and A5 are nitrogen atoms)
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
30 R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R3a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl, and
13
R4 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R4a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl.
[11] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above 5 [10], wherein
A4 is C(R4), and
A5 is C(R5).
[12] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [10], wherein
10 A4 is C(R4), and
A5 is a nitrogen atom.
[13] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [10], wherein
A4 is a nitrogen atom, and
15 A5 is C(R5).
[14] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [10] or [13], wherein
A4 is a nitrogen atom,
A5 is C(R5),
20 R3 is C1-C6 haloalkyl,
R5 is a hydrogen atom or C1-C6 alkyl,
R6 is a hydrogen atom, a halogen atom or C1-C6 alkyl,
each of Y1 and Y4 is a hydrogen atom,
Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
25 Y3 is a hydrogen atom or C1-C6 haloalkyl.
[15] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [2], wherein
Q is a ring represented by Q3,
A4 is a nitrogen atom or C(R4),
30 A5 is a nitrogen atom or C(R5),
(excluding a case where both A4 and A5 are nitrogen atoms),
R1 is C1-C6 alkyl,
14
R2 is a hydrogen atom,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6)alkylthio optionally substituted with R3a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl, and
R4 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 5 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R4a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl.
[16] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [15], wherein
10 A4 is C(R4), and
A5 is C(R5).
[17] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [15], wherein
A4 is C(R4), and
15 A5 is a nitrogen atom.
[18] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [15], wherein
A4 is a nitrogen atom, and
A5 is C(R5).
20 [19] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [15] or [18], wherein
A4 is a nitrogen atom,
A5 is C(R5),
R3 is C1-C6 haloalkyl,
25 R5 is a hydrogen atom,
R6 is a hydrogen atom,
Y1 is a hydrogen atom,
each of Y2 and Y3 is independently a hydrogen atom, a halogen atom or C1-C6
haloalkyl, and
30 Y4 is a hydrogen atom or a halogen atom.
[20] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [2], wherein Q is a ring represented by Q4.
15
[21] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [20], wherein
A8 is a nitrogen atom.
[22] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above 5 [20], wherein
A8 is C(R8).
[23] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [20], [21] or [22], wherein
R1 is C1-C6 alkyl,
10 R6 is a hydrogen atom,
R7 is C1-C6 haloalkyl,
R8 is a hydrogen atom or C1-C6 alkyl,
each of Y1 and Y4 is a hydrogen atom,
Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
15 Y3 is a hydrogen atom or C1-C6 haloalkyl.
[24] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [3], wherein
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
20 R3 is C1-C6 haloalkyl,
R4 is a hydrogen atom,
A1a is C1-C6 alkyl,
Y5 is a hydrogen atom, and
Y6 is C1-C6 haloalkyl.
25 [25] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [4], wherein
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
R3 is C1-C6 haloalkyl,
30 R4 is a hydrogen atom,
A1a is C1-C6 alkyl,
T1a is C1-C6 alkyl,
16
each of Y1, Y3 and Y4 is a hydrogen atom, and
Y2 is C1-C6 haloalkyl.
[26] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [2], wherein
A1 is N(A1a) or 5 an oxygen atom,
R2 is a hydrogen atom,
R3 is C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl,
R4 is a hydrogen atom,
10 R5 is a hydrogen atom or C1-C6 alkyl,
R6 is a hydrogen atom,
A1a is C1-C6 alkyl,
each of Y1 and Y4 is a hydrogen atom, and
each of Y2 and Y3 is independently a hydrogen atom or C1-C6 haloalkyl.
15 [27] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-A-A1), (1-AB1),
(1-A-C1), (1-A-D1), (1-A-E1), (1-A-F1), (1-A-G1), (1-A-H1), (1-A-I1), (1-A-J1), (1-AK1),
(1-A-L1), (1-A-M1) or (1-A-N1):
17
18
[28] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1] or [3], wherein the formula (1) is the folloinwg formula (1-B-A1):
5
[29] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1] or [4], wherein the formula (1) is the folloinwg formula (1-C-A1):
19
[30] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], wherein the formula (1) is the folloinwg formula (1-d-A1):
5 wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
10 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
A1a is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and
each of R2, R4, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
C1-C6 alkyl or C1-C6 haloalkyl.
[31] The condensed heterocyclic compound or its salt or an N-oxide thereof according
15 to the above [30], wherein
each of R1 and A1a is independently C1-C6 alkyl,
each of R3 and Y3 is independently C1-C6 haloalkyl, and
each of R2, R4, Y2 and Y4 is a hydrogen atom.
[32] The condensed heterocyclic compound or its salt or an N-oxide thereof according
20 to the above [1], wherein the formula (1) is the folloinwg formula (1-e-A1):
20
wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, 5 C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
A1a is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and
each of R2, R4, Y1, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
10 C1-C6 alkyl or C1-C6 haloalkyl.
[33] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [32], wherein
each of R1 and A1a is independently C1-C6 alkyl,
each of R3 and Y3 is independently C1-C6 haloalkyl, and
15 each of R2, R4, Y1 and Y4 is a hydrogen atom.
[34] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], wherein the formula (1) is the folloinwg formula (1-f-A1):
wherein
20 R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
21
haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
A1a is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and
each of R2, R4, Y1, Y2 and Y4 is independently a hydrogen atom, a halogen atom,
C1-C6 alkyl or C1-C6 haloalkyl.
[35] The condensed heterocyclic compound or its salt or an N-oxide 5 thereof according
to the above [34], wherein
each of R1 and A1a is independently C1-C6 alkyl,
R3 is C1-C6 haloalkyl,
each of R2, R4, Y1 and Y4 is a hydrogen atom, and
10 Y2 is a hydrogen atom or a halogen atom.
[36] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], wherein the formula (1) is the folloinwg formula (1-g-A1):
wherein
15 R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
20 A1a is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and
each of R2, R4, Y1, Y2 and Y3 is independently a hydrogen atom, a halogen atom,
C1-C6 alkyl or C1-C6 haloalkyl.
[37] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [36], wherein
25 each of R1 and A1a is independently C1-C6 alkyl,
R3 is C1-C6 haloalkyl,
each of R2, R4, Y1 and Y3 is a hydrogen atom, and
22
Y2 is a halogen atom or C1-C6 haloalkyl.
[38] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], wherein the formula (1) is the folloinwg formula (1-a-G1):
5 wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
10 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
A1a is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, and
each of R4, R5, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen
atom, C1-C6 alkyl or C1-C6 haloalkyl.
[39] The condensed heterocyclic compound or its salt or an N-oxide thereof according
15 to the above [38], wherein
each of R1 and A1a is independently C1-C6 alkyl,
each of R3 and Y3 is independently C1-C6 haloalkyl, and
each of R4, R5, Y1, Y2 and Y4 is a hydrogen atom.
[40] The condensed heterocyclic compound or its salt or an N-oxide thereof according
20 to the above [1], wherein the formula (1) is the folloinwg formula (1-a-I1):
wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
23
or C2-C6 haloalkynyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
A1a is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or 5 C2-C6 alkynyl, and
each of R2, R5, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen
atom, C1-C6 alkyl or C1-C6 haloalkyl.
[41] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [40], wherein
10 each of R1 and A1a is independently C1-C6 alkyl,
R4 is C1-C6 haloalkyl,
Y2 is a hydrogen atom or C1-C6 haloalkyl,
Y3 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
each of R2, R5, Y1 and Y4 is a hydrogen atom.
15 [42] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], wherein the formula (1) is the folloinwg formula (1-a-F1):
wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
20 or C2-C6 haloalkynyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, and
each of R2, R5, R6, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a
25 halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.
[43] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [42], wherein
24
R1 is C1-C6 alkyl,
R4 is C1-C6 haloalkyl,
each of Y2 and Y3 is independently a hydrogen atom or C1-C6 haloalkyl, and
each of R2, R5, R6, Y1 and Y4 is a hydrogen atom.
[44] The condensed heterocyclic compound or its salt or an N-oxide 5 thereof according
to the above [1], wherein the formula (1) is the folloinwg formula (1-a-O1):
wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
10 or C2-C6 haloalkynyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, and
each of R3, R5, R6, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a
15 halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.
[45] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [44], wherein
R1 is C1-C6 alkyl,
R4 is C1-C6 haloalkyl,
20 each of R6 and Y2 is independently a halogen atom, and
each of R3, R5, Y1, Y3 and Y4 is a hydrogen atom.
[46] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-a-b1):
25
wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
each of R3 and R4 is independently a hydrogen atom, a halogen 5 atom, C1-C6 alkyl,
C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-
C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
and
each of R2, R5, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen
10 atom, C1-C6 alkyl or C1-C6 haloalkyl.
[47] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [46], wherein
R1 is C1-C6 alkyl,
R3 is C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl,
15 each of Y2 and Y3 is independently a hydrogen atom or C1-C6 haloalkyl, and
each of R2, R4, R5, Y1 and Y4 is a hydrogen atom.
[48] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-a-b2):
20 wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
each of R3 and R4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl,
26
C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-
C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl,
and
each of R2, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
C1-C6 alkyl 5 or C1-C6 haloalkyl.
[49] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [48], wherein
R1 is C1-C6 alkyl,
each of R3 and Y3 is independently C1-C6 haloalkyl, and
10 each of R2, R4, Y1, Y2 and Y4 is a hydrogen atom.
[50] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1] or [2], wherein the formula (1) is the folloinwg formula (1-a-m2):
wherein
15 R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl
or C2-C6 haloalkynyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-C6 haloalkylsulfonyl, and
20 each of R2, R4, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen
atom, C1-C6 alkyl or C1-C6 haloalkyl.
[51] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [50], wherein
R1 is C1-C6 alkyl,
25 each of R3 and Y3 is independently C1-C6 haloalkyl, and
each of R2, R4, Y1, Y2 and Y4 is a hydrogen atom.
[52] The condensed heterocyclic compound or its salt or an N-oxide thereof according
27
to the above [1], [2] or [5], wherein the formula (1) is the folloinwg formula (1-a-p1):
wherein
R1 is C1-C6 alkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-5 C6 haloalkylthio, C1-
C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl,
A1a is a hydrogen atom or C1-C6 alkyl, and
each of R2, R5, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen
10 atom, C1-C6 alkyl or C1-C6 haloalkyl.
[53] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [52], wherein
each of R2 and R5 is independently a hydrogen atom or a halogen atom,
each of R3 and R4 is independently a hydrogen atom or C1-C6 haloalkyl,
15 Y3 is C1-C6 haloalkyl, and
each of Y1, Y2 and Y4 is a hydrogen atom.
[54] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], [2] or [5], wherein the formula (1) is the folloinwg formula (1-a-q1):
20 wherein
R1 is C1-C6 alkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-
C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl,
28
A1a is a hydrogen atom or C1-C6 alkyl, and
each of R2, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
C1-C6 alkyl or C1-C6 haloalkyl.
[55] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the 5 above [54], wherein
each of R3 and Y2 is independently C1-C6 haloalkyl,
A1a is C1-C6 alkyl, and
each of R2, Y1, Y3 and Y4 is a hydrogen atom.
[56] The condensed heterocyclic compound or its salt or an N-oxide thereof according
10 to the above [1], [2], [10] or [11], wherein the formula (1) is the folloinwg formula (1-a-
E1):
wherein
R1 is C1-C6 alkyl,
15 R2 is a hydrogen atom,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-
C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
each of R5, R6, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen
20 atom, C1-C6 alkyl or C1-C6 haloalkyl.
[57] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [56], wherein
each of R3, R4, Y2 and Y3 is independently a hydrogen atom or C1-C6 haloalkyl,
and
25 each of R5, R6, Y1 and Y4 is a hydrogen atom.
[58] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], [2], [10] or [12], wherein the formula (1) is the folloinwg formula (1-a29
D1):
wherein
R1 is C1-C6 alkyl,
R2 5 is a hydrogen atom,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-
C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
each of R6, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
10 C1-C6 alkyl or C1-C6 haloalkyl.
[59] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [58], wherein
R3 is C1-C6 haloalkyl,
Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl,
15 Y3 is a hydrogen atom or C1-C6 haloalkyl, and
each of R4, R6, Y1 and Y4 is a hydrogen atom.
[60] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], [2], [15] or [16], wherein the formula (1) is the folloinwg formula (1-a-j1):
20 wherein
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
30
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-
C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
each of R5, R6, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen
atom, C1-C6 alkyl 5 or C1-C6 haloalkyl.
[61] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [60], wherein
each of R3 and Y3 is independently C1-C6 haloalkyl, and
each of R4, R5, R6, Y1, Y2 and Y4 is a hydrogen atom.
10 [62] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [1], [2], [15] or [17], wherein the formula (1) is the folloinwg formula (1-a-j2):
wherein
R1 is C1-C6 alkyl,
15 R2 is a hydrogen atom,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-
C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
each of R6, Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
20 C1-C6 alkyl or C1-C6 haloalkyl.
[63] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [62], wherein
R3 is C1-C6 haloalkyl,
Y2 is a hydrogen atom or a halogen atom,
25 Y3 is a hydrogen atom or C1-C6 haloalkyl, and
each of R4, R6, Y1 and Y4 is a hydrogen atom.
[64] The condensed heterocyclic compound or its salt or an N-oxide thereof according
31
to the above [1], wherein
D substituted with -S(O)nR1 is a ring represented by either D1 or D2,
Q is a ring represented by either Q1 or Q2,
R1a is C1-C8 alkoxycarbonyl,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, 5 C1-C8 alkoxy
or C1-C8 haloalkoxy,
each of R3 and R4 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl,
C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-
C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl,
10 mercapto, cyano or nitro,
R5 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R6 is a hydrogen atom, a halogen atom or C1-C6 alkyl,
A1a is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6
haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6
15 halocycloalkyl (C1-C6) alkyl, and
each of Y1, Y2, Y3, Y4, Y5 and Y6 is independently a hydrogen atom, a halogen
atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, cyano or nitro.
[65] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [2], wherein
20 D substituted with -S(O)nR1 is a ring represented by D1,
G1 is C(Y1),
G2 is C(Y2),
G3 is C(Y3),
G4 is C(Y4),
25 A1 is N(A1 a ) or an oxygen atom,
A2 is C(R2 ),
A3 is C(R3 ),
each of R1 and A1 a is independently C1 -C6 alkyl,
R3 is C1 -C6 haloalkyl, C1 -C6 haloalkylthio, C1 -C6 haloalkylsulfinyl or C1 -C6
30 haloalkylsulfonyl,
R5 is a hydrogen atom or C1 -C6 alkyl,
each of Y2 and Y3 is independently a hydrogen atom or C1 -C6 haloalkyl, and
32
each of R2 , R4 , R6 , Y1 and Y4 is a hydrogen atom.
[66] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to the above [3], wherein
D substituted with -S(O)nR1 is a ring represented by D2,
Q is a ring 5 represented by Q1,
G5 is C(Y5),
A1 is N(A1 a ),
A2 is C(R2 ),
A3 is C(R3 ),
10 A4 is C(R4 ),
A5 is a nitrogen atom,
each of R1 and A1 a is independently C1 -C6 alkyl,
each of R2 , R4 and Y5 is a hydrogen atom, and
each of R3 and Y6 is independently C1 -C6 haloalkyl.
15 [67] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [66], wherein
R1 is C1 -C6 alkyl, C1 -C6 haloalkyl, C2 -C6 alkenyl, C2 -C6 haloalkenyl, C2 -C6
alkynyl, C2 -C6 haloalkynyl, C3 -C6 cycloalkyl (C1 -C6 ) alkyl or C3 -C6 halocycloalkyl (C1 -
C6 ) alkyl.
20 [68] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [66], wherein
R1 is C1-C6 alkyl, C1-C6 haloalkyl or C3 -C6 cycloalkyl (C1-C6) alkyl.
[69] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [66], wherein
25 R1 is C1-C6 alkyl or C1-C6 haloalkyl.
[70] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [66], wherein
R1 is C1-C6 alkyl.
[71] The condensed heterocyclic compound or its salt or an N-oxide thereof according
30 to any one of the above [1] to [66], wherein
R1 is C1-C6 haloalkyl.
[72] The condensed heterocyclic compound or its salt or an N-oxide thereof according
33
to any one of the above [1] to [71], wherein
R1a is C1-C8 alkoxy, C1-C8 alkoxycarbonyl or cyano.
[73] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [71], wherein
R1 a is C1 5 -C8 alkoxycarbonyl.
[74] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [73], wherein
R2 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[75] The condensed heterocyclic compound or its salt or an N-oxide thereof according
10 to any one of the above [1] to [73], wherein
R2 is a hydrogen atom.
[76] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
R3 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8
15 alkoxy, C1 -C8 haloalkoxy, C1 -C6 alkylthio, C1 -C6 haloalkylthio, (C1 -C6 ) alkylthio
optionally substituted with R3 a , C1 -C6 alkylsulfinyl, C1 -C6 haloalkylsulfinyl, C1 -C6
alkylsulfonyl or C1 -C6 haloalkylsulfonyl.
[77] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
20 R3 is a hydrogen atom, a halogen atom, C1 -C6 haloalkyl, C1 -C6 alkylthio, (C1 -
C6 ) alkylthio optionally substituted with R3 a , C1 -C6 haloalkylthio, C1 -C6
haloalkylsulfinyl or C1 -C6 haloalkylsulfonyl.
[78] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
25 R3 is a hydrogen atom, a halogen atom, C1 -C6 haloalkyl, C1 -C6 haloalkylthio,
C1 -C6 haloalkylsulfinyl or C1 -C6 haloalkylsulfonyl.
[79] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
R3 is C1 -C6 haloalkylthio, C1 -C6 haloalkylsulfinyl or C1 -C6 haloalkylsulfonyl.
30 [80] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
R3 is a halogen atom.
34
[81] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
R3 is C1 -C6 haloalkyl.
[82] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] 5 to [75], wherein
R3 is C1 -C6 haloalkylthio.
[83] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
R3 is C1 -C6 haloalkylsulfinyl.
10 [84] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [75], wherein
R3 is C1 -C6 haloalkylsulfonyl.
[85] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [84], wherein
15 R4 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8
alkoxy, C1 -C8 haloalkoxy, C1 -C6 alkylthio, C1 -C6 haloalkylthio, (C1 -C6 ) alkylthio
optionally substituted with R4 a , C1 -C6 alkylsulfinyl, C1 -C6 haloalkylsulfinyl, C1 -C6
alkylsulfonyl or C1 -C6 haloalkylsulfonyl.
[86] The condensed heterocyclic compound or its salt or an N-oxide thereof according
20 to any one of the above [1] to [84], wherein
R4 is a hydrogen atom, a halogen atom, C1 -C6 haloalkyl, C1 -C6 alkylthio, (C1 -
C6 ) alkylthio optionally substituted with R4 a , C1 -C6 haloalkylthio, C1 -C6
haloalkylsulfinyl or C1 -C6 haloalkylsulfonyl.
[87] The condensed heterocyclic compound or its salt or an N-oxide thereof according
25 to any one of the above [1] to [84], wherein
R4 is a hydrogen atom, a halogen atom, C1 -C6 haloalkyl, C1 -C6 haloalkylthio,
C1 -C6 haloalkylsulfinyl or C1 -C6 haloalkylsulfonyl.
[88] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [84], wherein
30 R4 is a hydrogen atom.
[89] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [84], wherein
35
R4 is a halogen atom.
[90] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [84], wherein
R4 is C1 -C6 haloalkylthio, C1 -C6 haloalkylsulfinyl or C1 -C6 haloalkylsulfonyl.
[91] The condensed heterocyclic compound or its salt or an N-oxide 5 thereof according
to any one of the above [1] to [84], wherein
R4 is C1 -C6 haloalkyl.
[92] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [91], wherein
10 R5 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[93] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [91], wherein
R5 is a halogen atom.
[94] The condensed heterocyclic compound or its salt or an N-oxide thereof according
15 to any one of the above [1] to [91], wherein
R5 is a hydrogen atom.
[95] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [91], wherein
R5 is C1 -C6 alkyl.
20 [96] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [95], wherein
R6 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[97] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [95], wherein
25 R6 is a hydrogen atom.
[98] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [95], wherein
R6 is a halogen atom.
[99] The condensed heterocyclic compound or its salt or an N-oxide thereof according
30 to any one of the above [1] to [95], wherein
R6 is C1 -C6 alkyl.
[100] The condensed heterocyclic compound or its salt or an N-oxide thereof according
36
to any one of the above [1] to [99], wherein
R7 is a hydrogen atom, a halogen atom or C1 -C6 haloalkyl.
[101] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [99], wherein
R7 is 5 C1 -C6 haloalkyl.
[102] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [101], wherein
R8 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[103] The condensed heterocyclic compound or its salt or an N-oxide thereof according
10 to any one of the above [1] to [101], wherein
R8 is C1 -C6 alkyl.
[104] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [103], wherein
A1 a is a hydrogen atom, C1 -C6 alkyl, (C1 -C6 ) alkyl optionally substituted with
15 A1 a - a , C2 -C6 alkenyl, C2 -C6 alkynyl, C1 -C8 alkoxy, C3 -C6 cycloalkyl or C(O)R1 0 a .
[105] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [103], wherein
A1 a is a hydrogen atom, C1 -C6 alkyl, C2 -C6 alkenyl, C2 -C6 alkynyl or C3 -C6
cycloalkyl.
20 [106] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [103], wherein
A1 a is a hydrogen atom.
[107] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [103], wherein
25 A1 a is C1 -C6 alkyl.
[108] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [107], wherein
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
C1 -C6 alkyl, C1 -C6 haloalkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, (C2 -C6 ) alkynyl optionally
30 substituted with Yb , C1 -C8 alkoxy, C1 -C8 haloalkoxy, C1 -C6 alkylthio, C1 -C6
haloalkylthio, (C1 -C6 ) alkylthio optionally substituted with Ya , C1 -C6 alkylsulfinyl, C1 -C6
haloalkylsulfinyl, C1 -C6 alkylsulfonyl, C1 -C6 haloalkylsulfonyl, -C(O)R9 0 a , -
37
C(O)NHR9 0 b , -C(O)N(R9 0 c )R9 0 b , -C(O)OH, hydroxy, -OC(O)R9 0 e , -OS(O)2R9 0 f , -
NH2 , -NHR9 0 g , -N(R9 0 h )R9 0 g , mercapto, -SC(O)R9 0 i , -S(O)2NHR9 0 j , -
S(O)2N(R9 0 k )R9 0 j , -SF5 , cyano, nitro, phenyl, phenyl optionally substituted with Yc ,
heterocyclyl or heterocyclyl optionally substituted with Yc .
[109] The condensed heterocyclic compound or its salt or an N-oxide 5 thereof according
to any one of the above [1] to [107], wherein
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom,
C1 -C6 alkyl, C1 -C6 haloalkyl, C2 -C6 alkenyl, (C2 -C6 ) alkynyl optionally substituted with
Yb , C1 -C8 alkoxy, C1 -C6 alkylthio, C1 -C6 haloalkylthio, (C1 -C6 ) alkylthio optionally
10 substituted with Ya , C1 -C6 alkylsulfinyl, C1 -C6 alkylsulfonyl, -C(O)R9 0 a , -
C(O)N(R9 0 c )R9 0 b , -C(O)OH, -NH2 , -NHR9 0 g , -N(R9 0 h )R9 0 g , mercapto, cyano, nitro,
phenyl, phenyl optionally substituted with Yc , heterocyclyl or heterocyclyl optionally
substituted with Yc .
[110] The condensed heterocyclic compound or its salt or an N-oxide thereof according
15 to any one of the above [1] to [109], wherein
Y1 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[111] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [109], wherein
Y1 is a hydrogen atom.
20 [112] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [109], wherein
Y1 is a halogen atom.
[113] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [109], wherein
25 Y1 is C1 -C6 alkyl.
[114] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [109], wherein
Y1 is C1 -C6 haloalkyl.
[115] The condensed heterocyclic compound or its salt or an N-oxide thereof according
30 to any one of the above [1] to [114], wherein
Y2 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C2 -C6
alkenyl, (C2 -C6 ) alkynyl optionally substituted with Yb , C1 -C8 alkoxy, C1 -C6 alkylthio,
38
C1 -C6 haloalkylthio, (C1 -C6 ) alkylthio optionally substituted with Ya , C1 -C6 alkylsulfinyl,
C1 -C6 alkylsulfonyl, -NH2 , -NHR9 0 g , nitro, phenyl, phenyl optionally substituted with Yc
or heterocyclyl.
[116] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] 5 to [114], wherein
Y2 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[117] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [114], wherein
Y2 is a hydrogen atom.
10 [118] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [114], wherein
Y2 is a halogen atom.
[119] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [114], wherein
15 Y2 is C1 -C6 alkyl.
[120] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [114], wherein
Y2 is C1 -C6 haloalkyl.
[121] The condensed heterocyclic compound or its salt or an N-oxide thereof according
20 to any one of the above [1] to [120], wherein
Y3 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8
alkoxy, C1 -C6 alkylthio, (C1 -C6 ) alkylthio optionally substituted with Ya , C1 -C6
alkylsulfinyl, C1 -C6 alkylsulfonyl, -C(O)R9 0 a , -C(O)N(R9 0 c )R9 0 b , -C(O)OH, cyano or
nitro.
25 [122] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [120], wherein
Y3 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[123] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [120], wherein
30 Y3 is a hydrogen atom.
[124] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [120], wherein
39
Y3 is a halogen atom.
[125] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [120], wherein
Y3 is C1 -C6 alkyl.
[126] The condensed heterocyclic compound or its salt or an N-oxide 5 thereof according
to any one of the above [1] to [120], wherein
Y3 is C1 -C6 haloalkyl.
[127] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [126], wherein
10 Y4 is a hydrogen atom, a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8
alkoxy, C1 -C6 alkylthio, C1 -C6 alkylsulfonyl, -N(R9 0 h )R9 0 g or cyano.
[128] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [126], wherein
Y4 is C1 -C8 alkoxy, C1 -C6 alkylthio, C1 -C6 alkylsulfonyl, -N(R9 0 h )R9 0 g or cyano.
15 [129] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [126], wherein
Y4 is a hydrogen atom, a halogen atom, C1 -C6 alkyl or C1 -C6 haloalkyl.
[130] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [126], wherein
20 Y4 is a hydrogen atom.
[131] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [126], wherein
Y4 is a halogen atom.
[132] The condensed heterocyclic compound or its salt or an N-oxide thereof according
25 to any one of the above [1] to [126], wherein
Y4 is C1 -C6 alkyl.
[133] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [126], wherein
Y4 is C1 -C6 haloalkyl.
30 [134] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [133], wherein
Ya is C1 -C8 alkoxycarbonyl or C1 -C6 alkylcarbonyl.
40
[135] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [133], wherein
Ya is C1 -C8 alkoxycarbonyl.
[136] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] 5 to [135], wherein
Yb is C1 -C6 alkyl, C3 -C6 cycloalkyl, trimethylsilyl or phenyl.
[137] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [135], wherein
Yb is C3 -C6 cycloalkyl or trimethylsilyl.
10 [138] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [135], wherein
Yb is C3 -C6 cycloalkyl.
[139] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [135], wherein
15 Yb is trimethylsilyl.
[140] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [139], wherein
Yc is a halogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8 alkoxy, C1 -C8
haloalkoxy, cyano or nitro.
20 [141] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [139], wherein
Yc is a halogen atom or C1 -C6 haloalkyl.
[142] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [139], wherein
25 Yc is a halogen atom.
[143] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [139], wherein
Yc is C1 -C6 haloalkyl.
[144] The condensed heterocyclic compound or its salt or an N-oxide thereof according
30 to any one of the above [1] to [143], wherein
each of R1 0 a , R2 0 a , R3 0 a , R3 0 e , R4 0 a , R4 0 e , R5 0 a , R6 0 a and R9 0 a is
independently a hydrogen atom, C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C8 alkoxy or C1 -C8
41
haloalkoxy.
[145] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [143], wherein
each of R1 0 a , R2 0 a , R3 0 a , R3 0 e , R4 0 a , R4 0 e , R5 0 a , R6 0 a and R9 0 a is
independently a hydrogen atom, C1 -C6 alkyl 5 or C1 -C8 alkoxy.
[146] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [143], wherein
each of R1 0 a , R2 0 a , R3 0 a , R3 0 e , R4 0 a , R4 0 e , R5 0 a , R6 0 a and R9 0 a is a
hydrogen atom.
10 [147] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [143], wherein
each of R1 0 a , R2 0 a , R3 0 a , R3 0 e , R4 0 a , R4 0 e , R5 0 a , R6 0 a and R9 0 a is
independently C1 -C6 alkyl.
[148] The condensed heterocyclic compound or its salt or an N-oxide thereof according
15 to any one of the above [1] to [143], wherein
each of R1 0 a , R2 0 a , R3 0 a , R3 0 e , R4 0 a , R4 0 e , R5 0 a , R6 0 a and R9 0 a is
independently C1 -C8 alkoxy.
[149] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [148], wherein
20 each of R2 0 g , R2 0 h , R3 0 f , R3 0 g , R3 0 h , R3 0 i , R4 0 f , R4 0 g , R4 0 h , R4 0 i , R5 0 g ,
R5 0 h , R6 0 g , R6 0 h , R9 0 b , R9 0 c , R9 0 i , R9 0 j and R9 0 k is independently C1 -C6 alkyl or
C1 -C6 haloalkyl.
[150] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [148], wherein
25 each of R2 0 g , R2 0 h , R3 0 f , R3 0 g , R3 0 h , R3 0 i , R4 0 f , R4 0 g , R4 0 h , R4 0 i , R5 0 g ,
R5 0 h , R6 0 g , R6 0 h , R9 0 b , R9 0 c , R9 0 i , R9 0 j and R9 0 k is independently C1 -C6 alkyl.
[151] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [150], wherein
each of R9 0 g and R9 0 h is independently C1 -C6 alkyl, C1 -C6 haloalkyl, C1 -C6
30 alkylcarbonyl, C1 -C6 haloalkylcarbonyl, C1 -C8 alkoxycarbonyl, C1 -C8
haloalkoxycarbonyl, C1 -C6 alkylaminocarbonyl, C1 -C6 haloalkylaminocarbonyl, C1 -C6
alkylaminothiocarbonyl, C1 -C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1 -C6
42
alkylsulfonyl, C1 -C6 haloalkylsulfonyl, C1 -C6 alkylaminosulfonyl or di(C1 -C6 )
alkylaminosulfonyl.
[152] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [151], wherein
R9 0 g is C1 -C6 alkyl, C1 -C6 haloalkylcarbonyl, C1 5 -C8 alkoxycarbonyl or
phenylcarbonyl.
[153] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [151], wherein
R9 0 g is C1 -C6 alkyl.
10 [154] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [151], wherein
R9 0 g is C1 -C6 haloalkylcarbonyl.
[155] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [151], wherein
15 R9 0 g is C1 -C8 alkoxycarbonyl.
[156] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [151], wherein
R9 0 g is phenylcarbonyl.
[157] The condensed heterocyclic compound or its salt or an N-oxide thereof according
20 to any one of the above [1] to [156], wherein
R9 0 h is C1 -C6 alkyl.
[158] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [157], wherein
T1 is a sulfur atom.
25 [159] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [157], wherein
T1 is N(T1 a ).
[160] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [159], wherein
30 T1 a is a hydrogen atom.
[161] The condensed heterocyclic compound or its salt or an N-oxide thereof according
to any one of the above [1] to [159], wherein
43
T1 a is C1 -C6 alkyl.
[162] A pesticide containing one or more members selected from the condensed
heterocyclic compounds and their salts as defined in the above [1] to [161] as active
ingredient(s).
[163] An agricultural chemical containing one or more members 5 selected from the
condensed heterocyclic compounds and their salts as defined in the above [1] to [161]
as active ingredient(s).
[164] A parasiticide against internal or external parasites in or on a mammal or bird,
containing one or more members selected from the condensed heterocyclic compounds
10 and their salts as defined in the above [1] to [161] as activie ingredient(s).
[165] The parasiticide according to the above [164], wherein the external parasites are
Siphonaptera or ticks.
[166] An insecticide or acaricide containing one or more members selected from the
condensed heterocyclic compounds and their salts as defined in the above [1] to [161]
15 as active ingredient(s).
[167] A seed treatment agent containing one or more members selected from the
condensed heterocyclic compounds and their salts as defined in the above [1] to [161]
as active ingredient(s).
[168] The seed treatment agent according to the above [167], which is used to treat
20 seeds by dipping.
[169] A soil treatement agent containing one or more members selected from the
condensed hetercyclic compounds as defined in the above [1] to [161] as active
ingredient(s).
[170] The soil treatment agent according to the above [169], which is used to treat soil
25 by irrigation.
ADVANTAGEOUS EFFECTS OF INVENTION
The compounds of the present invention have excellent insecticidal and acaricidal
activities on many agricultural pest insects, spider mites, internal or external parasites in
30 or on a mammal or bird 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
44
persistence and are environmentally friendly. Thus, the present invention can provide
useful novel pesticides.
DESCRIPTION OF EMBODIMENTS
The compounds of the present invention can have geometrical 5 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
10 the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, and
the present invention covers any optically active isomers and any racemates.
Further, the compounds of the present invention can have tautomers depending
on the type of substituents in them, and the present invention covers all tautomers and
mixtures containing them in any ratios.
15 Some of the compounds of the present invention can be converted, by ordinary
methods, to 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 acids such as
methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid,
20 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 and
aspartic acid, with alkali metals such as lithium, sodium and potassium, with alkaline
25 earth metals such as calcium, barium and magnesium, with aluminum, and with
quaternary ammonium such as tetramethylammonium, tetrabutylammonium and
benzyltrimethylammonium.
In the present invention, the N-oxide is a compound having a nitrogen atom
constituting the ring in the heterocyclic group oxidized. A heterocyclic group which
30 may constitute an N-oxide may, for example, be a condensed ring containing a pyridine
ring, a condensed ring containing a pyrazine ring, a condensed ring containing a
pyridazine ring or a condensed ring containing a pyrimidine ring.
45
Next, specific examples of each substituent used herein will be given below. ndenotes
normal, i- iso, s- secondary, and tert- tertiary.
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 5 a halogen atom.
The expression “Ca-Cb alkyl” herein means a linear or branched hydrocarbon
group containing from a to b carbon atoms such as methyl, ethyl, n-propyl, i-propyl, nbutyl,
i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl or n-hexyl, and those within
the designated carbon number range are selected.
10 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
fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl,
15 trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl,
2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-
2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl,
2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2-
difluoropropyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl,
20 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-
trifluoro-1-(methyl)ethyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, 1,2,2,2-tetrafluoro-1-
(trifluoromethyl)ethyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl and
nonafluorobutyl, and those within the designated carbon number range are selected.
The expression “Ca-Cb alkenyl” herein means a linear or branched unsaturated
25 hydrocarbon group containing from a to b carbon atoms and having one or more double
bonds in the molecule, such as vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl,
2-methyl-2-propenyl, 3-methyl-2-butenyl or 1,1-dimethyl-2-propenyl, and those within
the designated carbon number range are selected.
The expression “Ca-Cb haloalkenyl” herein means a linear or branched
30 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
46
one another if two or more halogen atoms are present, such as 2,2-dichlorovinyl, 2-
fluoro-2-propenyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-
difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trifluoro-2-
propenyl, 2,3,3-trichloro-2-propenyl, 1-(trifluoromethyl)ethenyl, 4,4-difluoro-3-butenyl,
3,4,4-trifluoro-3-butenyl or 3-chloro-4,4,4-trifluoro-2-butenyl, and 5 those within the
designated carbon number range are selected.
The expression “Ca-Cb alkynyl” 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, such as ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-
10 hexynyl or 4,4,4-trifluoro-2-butynyl, and those within the designated carbon number
range are selected.
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
15 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 2-chloroethynyl, 2-
bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl or 3-iodo-2-
propynyl, and those within the designated carbon number range are selected.
The expression “Ca-Cb cycloalkyl” herein means a cyclic hydrocarbon group
20 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
number of carbon atoms does not exceed the designated carbon number range, such
as cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl,
cyclobutyl, cyclopentyl or cyclohexyl, and those within the designated carbon number
25 range are selected.
The expression “Ca-Cb halocycloalkyl” 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
number of carbon atoms does not exceed the designated carbon number range, in
30 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 another if two or more halogen atoms are present, such as 2,2-difluorocyclopropyl,
47
2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-
dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl or 2,2,3,3-
tetrafluorocyclobutyl, and those within the designated carbon number range are
selected.
The expression “Ca-Cb alkoxy” herein means an alkyl-O- group 5 in which the alkyl
is a previously mentioned alkyl group containing from a to b carbon atoms, such as
methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy
or 2-ethylhexyloxy, and those within the designated carbon number range are selected.
The expression “Ca-Cb haloalkoxy” herein means a haloalkyl-O- group in which the
10 haloalkyl is a previously mentioned haloalkyl group containing from a to b carbon atoms,
such as difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy,
2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2,-tetrafluoroethoxy, 2-chloro-
1,1,2-trifluoroethoxy or 1,1,2,3,3,3-hexafluoropropyloxy, and those within the designated
carbon number range are selected.
15 The expression “Ca-Cb alkenyloxy” herein means an alkenyl-O- group in which the
alkenyl is a previously mentioned alkenyl group containing from a to b carbon atoms,
such as 2-propenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy or 3-methyl-2-butenyloxy,
and those within the designated carbon number range are selected.
The expression “Ca-Cb haloalkenyloxy” herein means a haloalkenyl-O- group in
20 which the haloalkenyl is a previously mentioned haloalkenyl group containing from a to
b carbon atoms, such as 3,3-difluoroallyloxy or 3,3-dichloroallyloxy, and those within the
designated carbon number range are selected.
The expression “Ca-Cb alkynyloxy” herein means an alkynyl-O- group in which the
alkynyl is a previously mentioned alkynyl group containing from a to b carbon atoms,
25 such as ethynyloxy, propargyloxy, 2-butynyloxy, 1-pentynyloxy or 1-hexynyloxy, and
those within the designated carbon number range are selected.
The expression “Ca-Cb haloalkynyloxy” herein means a haloalkynyl-O- group in
which the haloalkynyl is a previously mentioned haloalkynyl group containing from a to b
carbon atoms, such as 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy or 3-iodo-2-
30 propynyloxy, and those within the designated carbon number range are selected.

CLAIMS
1. A condensed heterocyclic compound represented by the formula (1) or its salt or
an N-oxide thereof:
wherein D substituted with -S(O)nR1 is a ring represented by any one 5 of D1, D2 and D3:
Q is a ring represented by any one of Q1, Q2, Q3 and Q4:
G1 is a nitrogen atom or C(Y1),
10 G2 is a nitrogen atom or C(Y2),
G3 is a nitrogen atom or C(Y3),
G4 is a nitrogen atom or C(Y4),
G5 is a nitrogen atom or C(Y5),
T1 is N(T1a), an oxygen atom or a sulfur atom,
15 A1 is N(A1a), an oxygen atom or a sulfur atom,
A2 is a nitrogen atom or C(R2),
A3 is a nitrogen atom or C(R3),
A4 is a nitrogen atom or C(R4),
A5 is a nitrogen atom or C(R5),
324
A8 is a nitrogen atom or C(R8),
R1 is C1-C6 alkyl, C1-C6 haloalkyl, (C1-C6) alkyl optionally substituted with R1a, C2-
C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6
halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl, C3-C6 halocycloalkyl (C1-C6) alkyl or
hydroxy 5 (C1-C6) alkyl,
R1a is C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl or cyano,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
10 C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, -C(O)R20a, -C(O)OH, hydroxy, -NH2, -NHR20g, -N(R20h)R20g, mercapto,
cyano or nitro,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6
15 haloalkenyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6
halocycloalkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-
C6 haloalkylsulfonyl, -C(O)R30a, -C(O)OH, hydroxy, -OC(O)R30e, -OS(O)2R30f, -NH2, -
NHR30g, -N(R30h)R30g, mercapto, -SC(O)R30i, -SF5, cyano, nitro, phenyl, phenyl
20 optionally substituted with R3b, heterocyclyl or heterocyclyl optionally substituted with
R3b,
R3a is C1-C8 alkoxycarbonyl,
R3b is a halogen atom, a C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8
haloalkoxy, cyano or nitro,
25 R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6
haloalkenyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6
halocycloalkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-
C6 haloalkylsulfonyl, -C(O)R40a, -C(O)OH, hydroxy, -OC(O)R40e, -OS(O)2R40f, -NH2, -
30 NHR40g, -N(R40h)R40g, mercapto, -SC(O)R40i, -SF5, cyano, nitro, phenyl, phenyl
optionally substituted with R4b, heterocyclyl or heterocyclyl optionally substituted with
R4b,
325
R4a is C1-C8 alkoxycarbonyl,
R4b is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy,
cyano or nitro,
R5 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-5 C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, -C(O)R50a, -C(O)OH, hydroxy, -NH2, -NHR50g, -N(R50h)R50g, mercapto,
cyano or nitro,
R6 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
10 C1-C8 haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, -C(O)R60a, -C(O)OH, hydroxy, -NH2, -NHR60g, -N(R60h)R60g, mercapto,
cyano or nitro,
R7 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
15 C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, mercapto, -SF5, cyano or
nitro,
R8 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy or cyano,
20 A1a is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, (C1-C6) alkyl optionally
substituted with A1a-a, (C1-C6) haloalkyl optionally substituted with A1a-a, C2-C6 alkenyl,
C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-
C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl, C3-C6 halocycloalkyl
(C1-C6) alkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6
25 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C(O)R10a, hydroxy or
cyano,
A1a-a is C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C8
haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
30 haloalkylsulfonyl, hydroxy or cyano,
T1a is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6
haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C3-C6
326
cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl
(C1-C6) alkyl,
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-
C6 alkyl, C1-C6 haloalkyl, (C1-C6) alkyl optionally substituted with Ya, (C1-C6) haloalkyl
optionally substituted with Ya, C2-C6 alkenyl, C2-C6 haloalkenyl, 5 (C2-C6) alkenyl
optionally substituted with Ya, C2-C6 alkynyl, C2-C6 haloalkynyl, (C2-C6) alkynyl optionally
substituted with Yb, C1-C8 alkoxy, C1-C8 haloalkoxy, (C1-C8) alkoxy optionally substituted
with Ya, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, (C2-C6) alkenyloxy optionally
substituted with Ya, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy, (C2-C6) alkynyloxy
10 optionally substituted with Ya, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl
(C1-C6) alkyl, C3-C6 halocycloalkyl (C1-C6) alkyl, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with Ya, C2-C6 alkenylthio, C2-C6 haloalkenylthio, C2-
C6 alkynylthio, C2-C6 haloalkynylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, (C1-C6)
alkylsulfinyl optionally substituted with Ya, C2-C6 alkenylsulfinyl, C2-C6 haloalkenylsulfinyl,
15 C2-C6 alkynylsulfinyl, C2-C6 haloalkynylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, (C1-C6) alkylsulfonyl optionally substituted with Ya, C2-C6
alkenylsulfonyl, C2-C6 haloalkenylsulfonyl, C2-C6 alkynylsulfonyl, C2-C6
haloalkynylsulfonyl, -C(O)R90a, -C(O)NHR90b, -C(O)N(R90c)R90b, -C(O)OH, -
C(=NOR90d)R90a, -C(O)NH2, hydroxy, -OC(O)R90e, -OS(O)2R90f, -NH2, -NHR90g, -
20 N(R90h)R90g, mercapto, -SC(O)R90i, -S(O)2NHR90j, -S(O)2N(R90k)R90j, -SF5, cyano, nitro,
phenyl, phenyl optionally substituted with Yc, heterocyclyl or heterocyclyl optionally
substituted with Yc,
each of Y5 and Y6 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl,
C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-
25 C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl,
mercapto, -SF5, cyano or nitro,
Ya is C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C8
haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
30 haloalkylsulfonyl, hydroxy or cyano,
Yb is C1-C6 alkyl, C3-C6 cycloalkyl, trimethylsilyl or phenyl,
Yc is a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy,
327
cyano or nitro,
each of R10a, R20a, R30a, R30e, R40a, R40e, R50a, R60a and R90a is independently a
hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy or C1-C8 haloalkoxy,
each of R20g, R20h, R30f, R30g, R30h, R30i, R40f, R40g, R40h, R40i, R50g, R50h, R60g, R60h,
R90b, R90c, R90i, R90j and R90k is independently C1-C6 alkyl or 5 C1-C6 haloalkyl,
R90d is a hydrogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R90e is a hydrogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8
haloalkoxy, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1-C6) alkylamino or di(C1-C6)
haloalkylamino,
10 R90f is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylamino, C1-C6 haloalkylamino, di(C1-
C6) alkylamino or di(C1-C6) haloalkylamino,
each of R90g and R90h is independently C1-C6 alkyl, C1-C6 haloalkyl, C1-C6
alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 haloalkoxycarbonyl,
C1-C6 alkylaminocarbonyl, C1-C6 haloalkylaminocarbonyl, C1-C6 alkylaminothiocarbonyl,
15 C1-C6 haloalkylaminothiocarbonyl, phenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6
haloalkylsulfonyl, C1-C6 alkylaminosulfonyl or di(C1-C6) alkylaminosulfonyl, and
n is an integer of 0, 1 or 2.
2. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 1, wherein
20 D substituted with -S(O)nR1 is a ring represented by D1,
G1 is C(Y1),
G2 is C(Y2),
G3 is C(Y3),
G4 is C(Y4),
25 A2 is C(R2),
A3 is C(R3),
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl,
C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
30 R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
328
C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
C6 5 haloalkylsulfonyl,
each of R5, R6 and R8 is independently a hydrogen atom, a halogen atom, C1-C6
alkyl or C1-C6 haloalkyl,
R7 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl,
A1a is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A1a-a,
10 C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R10a,
A1a-a is C1-C8 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or
cyano,
R10a is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy,
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-
15 C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C2-C6) alkynyl optionally
substituted with Yb, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio,
(C1-C6) alkylthio optionally substituted with Ya, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl,
C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, -C(O)R90a, -C(O)NHR90b, -C(O)N(R90c)R90b,
-C(O)OH, hydroxy, -OC(O)R90e, -OS(O)2R90f, -NH2, -NHR90g, -N(R90h)R90g, mercapto, -
20 SC(O)R90i, -S(O)2NHR90j, -S(O)2N(R90k)R90j, -SF5, cyano, nitro, phenyl, phenyl optionally
substituted with Yc, heterocyclyl or heterocyclyl optionally substituted with Yc, and
Ya is C1-C8 alkoxycarbonyl.
3. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 1, wherein
25 D substituted with -S(O)nR1 is a ring represented by D2,
Q is a ring represented by Q1,
A1 is N(A1a),
A2 is C(R2),
A3 is C(R3),
30 A4 is C(R4),
A5 is a nitrogen atom,
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl,
329
C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-5 C6 alkylsulfonyl or C1-
C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
10 C6 haloalkylsulfonyl,
A1a is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A1a-a,
C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R10a,
A1a-a is C1-C8 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or
cyano,
15 R10a is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy,
Y5 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl, and
Y6 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl.
4. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 1, wherein
20 D substituted with -S(O)nR1 is a ring represented by D3,
Q is a ring represented by Q1,
G1 is C(Y1),
G2 is C(Y2),
G3 is C(Y3),
25 G4 is C(Y4),
T1 is N(T1 a ) or a sulfur atom,
A1 is N(A1 a )
A2 is C(R2),
A3 is C(R3),
30 A4 is C(R4 ),
A5 is a nitrogen atom,
R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl,
330
C2-C6 haloalkynyl, C3-C6 cycloalkyl (C1-C6) alkyl or C3-C6 halocycloalkyl (C1-C6) alkyl,
R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R3a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-5 C6 alkylsulfonyl or C1-
C6 haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, (C1-C6) alkylthio optionally
substituted with R4a, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl or C1-
10 C6 haloalkylsulfonyl,
A1a is a hydrogen atom, C1-C6 alkyl, (C1-C6) alkyl optionally substituted with A1a-a,
C2-C6 alkenyl, C2-C6 alkynyl, C1-C8 alkoxy, C3-C6 cycloalkyl or C(O)R10a,
A1a-a is C1-C8 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or
cyano,
15 R10a is a hydrogen atom, C1-C6 alkyl or C1-C8 alkoxy,
T1 a is a hydrogen atom or C1 -C6 alkyl, and
each of Y1, Y2, Y3 and Y4 is independently a hydrogen atom, a halogen atom, C1-
C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C6 alkylthio, C1-C6
haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
20 haloalkylsulfonyl, cyano or nitro.
5. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 2, wherein
Q is a ring represented by Q1,
A1 is N(A1 a ),
25 R1 is C1-C6 alkyl,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R3a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl,
R4 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
30 C6) alkylthio optionally substituted with R4a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl, and
A1 a is a hydrogen atom or C1 -C6 alkyl.
331
6. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 5, wherein
A4 is C(R4),
A5 is a nitrogen atom,
R2 is 5 a hydrogen atom,
R4 is a hydrogen atom or C1-C6 haloalkyl,
Y1 is a hydrogen atom, C1-C6 alkyl or C1-C6 haloalkyl,
Y2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6
alkenyl, (C2-C6) alkynyl optionally substituted with Yb, C1-C8 alkoxy, C1-C6 alkylthio, C1-
10 C6 haloalkylthio, (C1-C6) alkylthio optionally substituted with Ya, C1-C6 alkylsulfinyl, C1-C6
alkylsulfonyl, -NH2, -NHR90g, nitro, phenyl, phenyl optionally substituted with Yc,
thiophen-2-yl, pyridin-3-yl or pyridin-4-yl,
Y3 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C6 alkylthio, (C1-C6) alkylthio optionally substituted with Ya, C1-C6 alkylsulfinyl, C1-C6
15 alkylsulfonyl, -C(O)R90a, -C(O)N(R90c)R90b, -C(O)OH, cyano or nitro,
Y4 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C8 alkoxy,
C1-C6 alkylthio, C1-C6 alkylsulfonyl, -N(R90h)R90g or cyano,
Ya is C1-C8 alkoxycarbonyl,
Yb is C3-C6 cycloalkyl or trimethylsilyl,
20 Yc is a halogen atom or C1-C6 haloalkyl,
R90a is C1-C8 alkoxy,
each of R90b and R90c is independently C1-C6 alkyl,
R90g is C1-C6 alkyl, C1-C6 haloalkylcarbonyl, C1-C8 alkoxycarbonyl or
phenylcarbonyl, and
25 R90h is C1-C6 alkyl.
7. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 5, wherein
A4 is a nitrogen atom,
A5 is C(R5),
30 R2 is a hydrogen atom,
R3 is C1-C6 haloalkyl,
R5 is a hydrogen atom or C1-C6 alkyl,
332
Y1 is a hydrogen atom,
Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl,
Y3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl or cyano, and
Y4 is a hydrogen atom, a halogen atom or C1-C8 alkoxy.
8. The condensed heterocyclic compound or its salt or an N-oxide 5 thereof according
to Claim 2, wherein
Q is a ring represented by Q2,
A4 is a nitrogen atom or C(R4),
A5 is a nitrogen atom or C(R5),
10 (excluding a case where both A4 and A5 are nitrogen atoms)
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R3a, C1-C6 haloalkylsulfinyl or C1-C6
15 haloalkylsulfonyl, and
R4 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R4a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl.
9. The condensed heterocyclic compound or its salt or an N-oxide thereof according
20 to Claim 8, wherein
A4 is a nitrogen atom,
A5 is C(R5),
R3 is C1-C6 haloalkyl,
R5 is a hydrogen atom or C1-C6 alkyl,
25 R6 is a hydrogen atom, a halogen atom or C1-C6 alkyl,
each of Y1 and Y4 is a hydrogen atom,
Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
Y3 is a hydrogen atom or C1-C6 haloalkyl.
10. The condensed heterocyclic compound or its salt or an N-oxide thereof according
30 to Claim 2, wherein
Q is a ring represented by Q3,
A4 is a nitrogen atom or C(R4),
333
A5 is a nitrogen atom or C(R5),
(excluding a case where both A4 and A5 are nitrogen atoms),
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
R3 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 5 haloalkylthio, (C1-
C6)alkylthio optionally substituted with R3a, C1-C6 haloalkylsulfinyl or C1-C6
haloalkylsulfonyl, and
R4 is a hydrogen atom, a halogen atom, C1-C6 haloalkyl, C1-C6 haloalkylthio, (C1-
C6) alkylthio optionally substituted with R4a, C1-C6 haloalkylsulfinyl or C1-C6
10 haloalkylsulfonyl.
11. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 10, wherein
A4 is a nitrogen atom,
A5 is C(R5),
15 R3 is C1-C6 haloalkyl,
R5 is a hydrogen atom,
R6 is a hydrogen atom,
Y1 is a hydrogen atom,
each of Y2 and Y3 is independently a hydrogen atom, a halogen atom or C1-C6
20 haloalkyl, and
Y4 is a hydrogen atom or a halogen atom.
12. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 2, wherein Q is a ring represented by Q4.
13. The condensed heterocyclic compound or its salt or an N-oxide thereof according
25 to Claim 12, wherein
R1 is C1-C6 alkyl,
R6 is a hydrogen atom,
R7 is C1-C6 haloalkyl,
R8 is a hydrogen atom or C1-C6 alkyl,
30 each of Y1 and Y4 is a hydrogen atom,
Y2 is a hydrogen atom, a halogen atom or C1-C6 haloalkyl, and
Y3 is a hydrogen atom or C1-C6 haloalkyl.
334
14. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 3, wherein
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
R3 5 is C1-C6 haloalkyl,
R4 is a hydrogen atom,
A1a is C1-C6 alkyl,
Y5 is a hydrogen atom, and
Y6 is C1-C6 haloalkyl.
10 15. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 4, wherein
R1 is C1-C6 alkyl,
R2 is a hydrogen atom,
R3 is C1-C6 haloalkyl,
15 R4 is a hydrogen atom,
A1a is C1-C6 alkyl,
T1a is C1-C6 alkyl,
each of Y1, Y3 and Y4 is a hydrogen atom, and
Y2 is C1-C6 haloalkyl.
20 16. The condensed heterocyclic compound or its salt or an N-oxide thereof according
to Claim 2, wherein
A1 is N(A1a) or an oxygen atom,
R2 is a hydrogen atom,
R3 is C1-C6 haloalkyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl or C1-C6
25 haloalkylsulfonyl,
R4 is a hydrogen atom,
R5 is a hydrogen atom or C1-C6 alkyl,
R6 is a hydrogen atom,
A1a is C1-C6 alkyl,
30 each of Y1 and Y4 is a hydrogen atom, and
each of Y2 and Y3 is independently a hydrogen atom or C1-C6 haloalkyl.
17. A pesticide containing one or more members selected from the condensed heterocyclic compounds and their salts as defined in Claims 1 to 16 as active
ingredient(s).
18. An agricultural chemical containing one or more members selected from the
condensed heterocyclic compounds and their salts as defined in Claims 1 to 16 as
active ingredient(s).
19. A parasiticide against internal or external parasites in or on a mammal or bird,
containing one or more members selected from the condensed heterocyclic compounds
and their salts as defined in Claims 1 to 16 as activie ingredient(s).
20. The parasiticide according to Claim 19, wherein the external parasites are
Siphonaptera or ticks.
21. An insecticide or acaricide containing one or more members selected from the
condensed heterocyclic compounds and their salts as defined in Claims 1 to 16 as
active ingredient(s).
22. A seed treatment agent containing one or more members selected from the
condensed heterocyclic compounds and their salts as defined in Claims 1 to 16 as
active ingredient(s).
23. The seed treatment agent according to Claim 22, which is used to treat seeds by
dipping.
24. A soil treatement agent containg one or more members selected from the
condensed hetercydic compounds as defined in Claims 1 to 16 as active ingredient(s).
25. The soil treatment agent according to Claim 24, which is used to treat soil by
irrigation.