# US 2019/0375765 A1 · Condensed heterocyclic compounds and pesticides

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- Number: US 2019/0375765 A1
- Document ID: US20190375765A1
- Status: Published application
- Kind: A1
- Application number: 16/545,594
- Filed: 2019-08-20
- Published: 2019-12-12
- Earliest claimed: 2015-02-12
- Assignees: Nissan Chemical Corporation
- Applicants: Nissan Chemical Corporation
- Inventors: Takao KUDO; Yukihiro MAIZURU; Ayano TANAKA; Kenkichi NOTO; Hiroto MATSUI; Masaki KOBAYASHI
- Web page: https://patentgrep.com/patent/US20190375765A1

## CPC

- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/5025: ortho- or peri-condensed with heterocyclic ring systems
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61P 33/00: Antiparasitic agents
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- C07D 471/04: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

To provide novel pesticides, especially insecticides or acaricides. 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, Q is a ring represented by any one of Q1, Q2, Q3 and Q4, 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, R1a is C1-C8 alkoxycarbonyl, and n is an integer of 0, 1 or 2.

## Claims

### Claim at position 1

1-25. (canceled)

### Claim at position 2

26: A condensed heterocyclic compound represented by the following formula or its salt or an N-oxide thereof:
wherein:
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);
A4 is a nitrogen atom or C(R4);
A5 is a nitrogen atom or C(R5);
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;
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-C6 alkoxy, 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 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 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;
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, —NHR40g, —N(R40h)R40g, mercapto, —SC(O)R40i, —SF5, cyano, nitro, phenyl, phenyl optionally substituted with R4b, heterocyclyl or heterocyclyl optionally substituted with R4b;
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 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 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;
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 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 (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 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, phenyl, phenyl optionally substituted with Yc, heterocyclyl or heterocyclyl optionally substituted with Y;
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 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, cyano or nitro;
each of 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;
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-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 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl or di(C1-C6) alkylaminosulfonyl; and
n is an integer of 0, 1 or 2.

### Claim at position 3 (depends on 26)

27: The condensed heterocyclic compound or its salt or an N-oxide thereof according to claim 26, wherein:
G1 is C(Y1);
G2 is C(Y2);
G3 is C(Y3);
G4 is C(Y4);
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;
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-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;
each of R5 and R6 is independently a hydrogen atom, a halogen atom, C1-C6 alkyl or C1-C6 haloalkyl;
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 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 substituted with Y, heterocyclyl or heterocyclyl optionally substituted with Yc; and
Ya is C1-C8 alkoxycarbonyl.

### Claim at position 4 (depends on 27)

28: The condensed heterocyclic compound or its salt or an N-oxide thereof according to claim 27, wherein:
A4 and A5 are not nitrogen atoms at the same time;
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
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.

### Claim at position 5 (depends on 28)

29: The condensed heterocyclic compound or its salt or an N-oxide thereof according to claim 28, wherein:
A4 is a nitrogen atom;
A5 is C(R5);
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 haloalkyl; and
Y4 is a hydrogen atom or a halogen atom.

### Claim at position 6 (depends on 27)

30: The condensed heterocyclic compound or its salt or an N-oxide thereof according to claim 27, wherein:
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;
R5 is a hydrogen atom or C1-C6 alkyl;
R6 is a hydrogen atom;
each of Y1 and Y4 is a hydrogen atom; and
each of Y2 and Y3 is independently a hydrogen atom or C1-C6 haloalkyl.

### Claim at position 7 (depends on 26)

31: The condensed heterocyclic compound or its salt or an N-oxide thereof according to claim 26, wherein:
G1 is C(Y1);
G2 is C(Y2);
G3 is C(Y3);
G4 is C(Y4);
A4 is a nitrogen atom;
A5 is C(R5); and
n is 2.

### Claim at position 8 (depends on 31)

32: The condensed heterocyclic compound or its salt or an N-oxide thereof according to claim 31, wherein:
each of Y1, Y2 and Y4 is a hydrogen atom;
Y3 is C1-C6 haloalkyl;
each of R2, R5 and R6 is a hydrogen atom; and
R3 is a C1-C6 haloalkyl.

### Claim at position 9 (depends on 26)

33: An agricultural chemical composition, comprising:
the condensed heterocyclic compound of claim 26 or its salt or N-oxide as an active ingredient; and
an agriculturally acceptable diluent.

### Claim at position 10 (depends on 26)

34: A method for treating internal or external parasites in or on a mammal or bird, comprising:
administering the condensed heterocyclic compound of claim 26 or its salt or N-oxide to the mammal or bird.

### Claim at position 11 (depends on 31)

35: The method according to claim 31, wherein the external parasites are Siphonaptera or ticks.

### Claim at position 12 (depends on 26)

36: A method for treating a seed, comprising:
applying the condensed heterocyclic compound of claim 26 or its salt or N-oxide to the seed.

### Claim at position 13 (depends on 26)

37: A method for treating soil, comprising:
applying the condensed heterocyclic compound of claim 26 or its salt or N-oxide to soil.