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

Patent Document 16: WO2014/123206

Patent Document 17: WO2014/123205

Patent Document 18: WO2014/104407

Patent Document 19: WO2013/180194

5 Patent Document 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,

and which has low persistence.

SOLUTION TO PROBLEMS

The present inventors have conducted extensive studies to achieve the above

5 object and as a result, found that a novel condensed 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),

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,

5 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),
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,

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
5 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, - 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

(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

5 haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-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,

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

5 haloalkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-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),

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,

5 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-
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

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),

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,

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,

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

5 phenylcarbonyl, 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

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

5 to the above [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,

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
5 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.
[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.

[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

5 to the above [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,

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
5 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

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-A- B1), (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-A- K1), (1-A-L1), (1-A-M1) or (1-A-N1):

(1-A-Bl)

R2 ( o):s"Rl

R•l

......N

n G
f N"' G2

N G3
G4
Rs R6
(1-A-Et)

R6

(1-A-Ll)

(1-A-M1)

[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):
( Rt

R N j)-v•
NjJ N S
Ala

(1-B-Al)
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):

[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):

wherein

R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl,
5 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,
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

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.
5 [35] The condensed heterocyclic compound or its salt or an N-oxide 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

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

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,
5 A1a is a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl or 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

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.
5 [44] 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-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):

wherein

R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl or C2-C6 haloalkynyl,
5 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 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,

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,

5 C1-C6 alkyl 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

to the above [1], [2] or [5], wherein the formula (1) is the folloinwg formula (1-a-p1):

wherein

R1 is C1-C6 alkyl,

5 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, 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,

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

5 to the 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-a-

D1):

wherein

R1 is C1-C6 alkyl,

5 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,

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,

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

5 atom, C1-C6 alkyl 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

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,

5 R2 is a hydrogen atom, a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, 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

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)n R1 is a ring represented by D2,

5 Q is a ring 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

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
5 R1 a is C1 -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.

[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

5 to any one of the above [1] 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

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.

5 [91] 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 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

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
5 R7 is 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 , -

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)2 R9 0 f , - NH2 , -NHR9 0 g , -N(R9 0 h )R9 0 g , mercapto, -SC(O)R9 0 i , -S(O)2 NHR9 0 j , -
S(O)2 N(R9 0 k )R9 0 j , -SF5 , cyano, nitro, phenyl, phenyl optionally substituted with Yc , heterocyclyl or heterocyclyl optionally substituted with Yc .
5 [109] 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 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,

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

5 to any one of the above [1] 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

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.

5 [126] 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 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.

[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

5 to any one of the above [1] 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

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

5 independently a hydrogen atom, C1 -C6 alkyl 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

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
5 R9 0 g is C1 -C6 alkyl, C1 -C6 haloalkylcarbonyl, C1 -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

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).
5 [163] An agricultural chemical 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).
[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

persistence and are environmentally friendly. Thus, the present invention can provide

useful novel pesticides.

DESCRIPTION OF EMBODIMENTS

5 The compounds of the present invention can have geometrical isomers such as E- isomers 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.

Next, specific examples of each substituent used herein will be given below. n- denotes 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
5 expression “halo” also means such 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, n- butyl, 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

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,
5 3,4,4-trifluoro-3-butenyl or 3-chloro-4,4,4-trifluoro-2-butenyl, and 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.

claims

1. A compound represented by the formula (Z-1}: Et
(4n
(Z-1)
wherein Gh is C(Y1); 5 GaisC(Y2),
' Ga is C(Y3), G4isC(Y4), Y1 Is a hydrogen atom,
Y2 Is a hydrogen atom, a halogen atom, C-i-Cb alkyl, Ci-Co haloalkyl, Ci-Ca alkoxy, 10 cyano, -NH2 or nltro,
Y3 is a hydrogen atom, a halogen atom, C-i-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, cyano, -NH2 ornitro,
Y4 Is a hydrogen atom or a halogen atom, J1 is a hydrogen atom, methyl or ethyl, and 15 n is an Integer of 0,1 or 2.
2. The compound according to Claim 1, wherein n is 0.
3. The compound according to Claim 2, wherein
Y2 Is a hydrogen atom, a halogen atom, Ct-Cs haloalkyl, Ci-Cs alkoxy or nitro, and 20 Y3 Is a a hydrogen atom, a halogen atom or Ci-Cs haloalkyl