IP Library › Granted Patent US 11,787,809
Granted Patent B2
US 11,787,809 · App. 16/967,199 · Granted Oct 17, 2023

Oxime group-containing condensed heterocyclic compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide

Inventors: Yusuke Sano (Osaka, JP); Ikki Yonemura (Osaka, JP); Soichiro Matsuo (Osaka, JP); Akiyuki Suwa (Osaka, JP); Shunpei Fujie (Osaka, JP)
Assignee: NIHON NOHYAKU CO., LTD.
C07D487/04A01N43/40A01N43/76A01N43/90C07D213/81C07D405/04C07D413/04C07D413/14C07D471/04
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Quick Facts
Patent No.
US 11,787,809
App. No.
16/967,199
Granted
Oct 17, 2023
Kind
B2
Abstract

Provided are an oxime group-containing condensed heterocyclic compound or a salt thereof, preferably a condensed heterocyclic compound represented by general formula (1): (wherein the symbols are defined in the specification); an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide.

Claims (314)

1. A condensed heterocyclic compound represented by formula (1):

wherein

R 1 represents

(a1) a (C 1 -C 6 ) alkyl group;

(a2) a (C 3 -C 6 ) cycloalkyl group;

(a3) a (C 2 -C 6 ) alkenyl group; or

(a4) a (C 2 -C 6 ) alkynyl group,

R 2 represents

(b1) a hydrogen atom;

(b2) a (C 1 -C 6 ) alkyl group;

(b3) a (C 3 -C 6 ) cycloalkyl group;

(b4) a halo (C 1 -C 6 ) alkyl group;

(b5) an amino group;

(b6) a cyano group;

(b7) a (C 1 -C 6 ) alkoxycarbonyl group;

(b8) an aminocarbonyl group;

(b9) a mono-(C 1 -C 6 ) alkylaminocarbonyl group; or

(b10) a di-(C 1 -C 6 ) alkylaminocarbonyl group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c4) a (C 2 -C 6 ) alkynyl group;

(c5) a (C 3 -C 6 ) cycloalkyl group;

(c6) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c8) a halo (C 1 -C 6 ) alkyl group;

(c9) a halo (C 2 -C 6 ) alkenyl group;

(c10) a halo (C 2 -C 6 ) alkynyl group;

(c11) a phenyl group;

(c12) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group;

(c13) a phenyl (C 1 -C 6 ) alkyl group;

(c14) a phenyl (C 1 -C 6 ) alkyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group;

(c15) a (C 1 -C 6 ) alkylcarbonyl group;

(c16) a (C 3 -C 6 ) cycloalkylcarbonyl group;

(c17) a cyanoalkyl group;

(c18) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(c19) a (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group;

(c20) a (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group;

(c21) a halo (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;

(c22) a halo (C 1 -C 6 ) alkylsulfinyl (C 1 -C 6 ) alkyl group; or

(c23) a halo (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkyl group,

R 4 represents

(d1) a halogen atom;

(d2) a cyano group;

(d3) a nitro group;

(d4) a (C 1 -C 6 ) alkyl group;

(d5) a (C 1 -C 6 ) alkoxy group;

(d6) a (C 2 -C 6 ) alkenyloxy group;

(d7) a (C 2 -C 6 ) alkynyloxy group;

(d8) a halo (C 1 -C 6 ) alkyl group;

(d9) a halo (C 1 -C 6 ) alkoxy group;

(d10) a halo (C 2 -C 6 ) alkenyloxy group;

(d11) a halo (C 2 -C 6 ) alkynyloxy group;

(d12) a (C 1 -C 6 ) alkylthio group;

(d13) a (C 1 -C 6 ) alkylsulfinyl group;

(d14) a (C 1 -C 6 ) alkylsulfonyl group;

(d15) a halo (C 1 -C 6 ) alkylthio group;

(d16) a halo (C 1 -C 6 ) alkylsulfinyl group; or

(d17) a halo (C 1 -C 6 ) alkylsulfonyl group,

A, A 2 and A 3 each represent CH or a nitrogen atom,

A 1 represents O, S or N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group; (e2) a (C 3 -C 6 ) cycloalkyl group; (e3) a (C 2 -C 6 ) alkenyl group; or (e4) a (C 2 -C 6 ) alkynyl group),

m represents 0, 1 or 2, and

n represents 0, 1 or 2, or

a salt thereof.

2. The condensed heterocyclic compound according to claim 1 or a salt thereof, wherein the condensed heterocyclic compound is represented by formula (1A):

wherein

R 1 represents (a1) a (C 1 -C 6 ) alkyl group,

R 2 represents

(b1) a hydrogen atom; or

(b2) a (C 1 -C 6 ) alkyl group,

R 3 represents

(c1) a hydrogen atom; or

(c8) a halo (C 1 -C 6 ) alkyl group,

R 4 represents

(d8) a halo (C 1 -C 6 ) alkyl group;

(d9) a halo (C 1 -C 6 ) alkoxy group;

(d15) a halo (C 1 -C 6 ) alkylthio group;

(d16) a halo (C 1 -C 6 ) alkylsulfinyl group; or

(d17) a halo (C 1 -C 6 ) alkylsulfonyl group,

A represents a nitrogen atom,

A 2 and A 3 each represent CH or a nitrogen atom,

A 1 represents O or N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group),

m represents 0 or 2, and

n represents 1.

3. The condensed heterocyclic compound according to claim 2 or a salt thereof, wherein A 1 is O.

4. An agricultural and horticultural insecticide comprising the condensed heterocyclic compound according to claim 1 or a salt thereof as an active ingredient.

5. A method for using an agricultural and horticultural insecticide, the method comprising applying an effective amount of the condensed heterocyclic compound according to claim 1 or a salt thereof to plants or soil.

6. An animal ectoparasite control agent comprising an effective amount of the condensed heterocyclic compound according to claim 1 or a salt thereof as an active ingredient.

7. The condensed heterocyclic compound according to claim 1 or a salt thereof, wherein the condensed heterocyclic compound is represented by formula (1):

wherein

R 1 represents

(a1) a (C 1 -C 6 ) alkyl group;

(a2) a (C 3 -C 6 ) cycloalkyl group;

(a3) a (C 2 -C 6 ) alkenyl group; or

(a4) a (C 2 -C 6 ) alkynyl group,

R 2 represents

(b1) a hydrogen atom;

(b2) a (C 1 -C 6 ) alkyl group;

(b3) a (C 3 -C 6 ) cycloalkyl group;

(b4) a halo (C 1 -C 6 ) alkyl group; or

(b5) an amino group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c4) a (C 2 -C 6 ) alkynyl group;

(c5) a (C 3 -C 6 ) cycloalkyl group;

(c6) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c8) a halo (C 1 -C 6 ) alkyl group;

(c9) a halo (C 2 -C 6 ) alkenyl group;

(c10) a halo (C 2 -C 6 ) alkynyl group;

(c11) a phenyl group;

(c12) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group;

(c13) a phenyl (C 1 -C 6 ) alkyl group;

(c14) a phenyl (C 1 -C 6 ) alkyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group;

(c15) a (C 1 -C 6 ) alkylcarbonyl group; or

(c16) a (C 3 -C 6 ) cycloalkylcarbonyl group,

R 4 represents

(d1) a halogen atom;

(d2) a cyano group;

(d3) a nitro group;

(d4) a (C 1 -C 6 ) alkyl group;

(d5) a (C 1 -C 6 ) alkoxy group;

(d6) a (C 2 -C 6 ) alkenyloxy group;

(d7) a (C 2 -C 6 ) alkynyloxy group;

(d8) a halo (C 1 -C 6 ) alkyl group;

(d9) a halo (C 1 -C 6 ) alkoxy group;

(d10) a halo (C 2 -C 6 ) alkenyloxy group;

(d11) a halo (C 2 -C 6 ) alkynyloxy group;

(d12) a (C 1 -C 6 ) alkylthio group;

(d13) a (C 1 -C 6 ) alkylsulfinyl group;

(d14) a (C 1 -C 6 ) alkylsulfonyl group;

(d15) a halo (C 1 -C 6 ) alkylthio group;

(d16) a halo (C 1 -C 6 ) alkylsulfinyl group; or

(d17) a halo (C 1 -C 6 ) alkylsulfonyl group,

A, A 2 and A 3 each represent CH or a nitrogen atom,

A 1 represents O, S or N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group; (e2) a (C 3 -C 6 ) cycloalkyl group; (e3) a (C 2 -C 6 ) alkenyl group; or (e4) a (C 2 -C 6 ) alkynyl group),

m represents 0, 1 or 2, and

n represents 0, 1 or 2.

8. The condensed heterocyclic compound according to claim 7 or a salt thereof, wherein the condensed heterocyclic compound is represented by formula (1A):

wherein

R 1 represents

(a1) a (C 1 -C 6 ) alkyl group;

(a2) a (C 3 -C 6 ) cycloalkyl group;

(a3) a (C 2 -C 6 ) alkenyl group; or

(a4) a (C 2 -C 6 ) alkynyl group,

R 2 represents

(b1) a hydrogen atom;

(b2) a (C 1 -C 6 ) alkyl group;

(b3) a (C 3 -C 6 ) cycloalkyl group; or

(b5) an amino group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c4) a (C 2 -C 6 ) alkynyl group;

(c5) a (C 3 -C 6 ) cycloalkyl group;

(c6) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c8) a halo (C 1 -C 6 ) alkyl group;

(c9) a halo (C 2 -C 6 ) alkenyl group;

(c10) a halo (C 2 -C 6 ) alkynyl group;

(c11) a phenyl group;

(c12) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group;

(c13) a phenyl (C 1 -C 6 ) alkyl group; or

(c14) a phenyl (C 1 -C 6 ) alkyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group,

R 4 represents

(d1) a halogen atom;

(d2) a cyano group;

(d3) a nitro group;

(d4) a (C 1 -C 6 ) alkyl group;

(d5) a (C 1 -C 6 ) alkoxy group;

(d6) a (C 2 -C 6 ) alkenyloxy group;

(d7) a (C 2 -C 6 ) alkynyloxy group;

(d8) a halo (C 1 -C 6 ) alkyl group;

(d9) a halo (C 1 -C 6 ) alkoxy group;

(d10) a halo (C 2 -C 6 ) alkenyloxy group;

(d11) a halo (C 2 -C 6 ) alkynyloxy group;

(d12) a (C 1 -C 6 ) alkylthio group;

(d13) a (C 1 -C 6 ) alkylsulfinyl group;

(d14) a (C 1 -C 6 ) alkylsulfonyl group;

(d15) a halo (C 1 -C 6 ) alkylthio group;

(d16) a halo (C 1 -C 6 ) alkylsulfinyl group; or

(d17) a halo (C 1 -C 6 ) alkylsulfonyl group,

A, A 2 and A 3 each represent CH or a nitrogen atom,

A 1 represents O, S or N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group; (e2) a (C 3 -C 6 ) cycloalkyl group; (e3) a (C 2 -C 6 ) alkenyl group; or (e4) a (C 2 -C 6 ) alkynyl group),

m represents 0, 1 or 2, and

n represents 0, 1 or 2.

9. The condensed heterocyclic compound according to claim 8 or a salt thereof, wherein

R 1 represents (a1) a (C 1 -C 6 ) alkyl group,

R 2 represents

(b1) a hydrogen atom; or

(b2) a (C 1 -C 6 ) alkyl group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c11) a phenyl group; or

(c13) a phenyl (C 1 -C 6 ) alkyl group,

R 4 represents

(d8) a halo (C 1 -C 6 ) alkyl group; or

(d15) a halo (C 1 -C 6 ) alkylthio group,

A, A 2 and A 3 each represent a nitrogen atom,

A 1 represents N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group),

m represents 0, 1 or 2, and

n represents 1.

10. The condensed heterocyclic compound according to claim 8 or a salt thereof, wherein

R 1 represents (a1) a (C 1 -C 6 ) alkyl group,

R 2 represents

(b1) a hydrogen atom; or

(b2) a (C 1 -C 6 ) alkyl group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c11) a phenyl group; or

(c13) a phenyl (C 1 -C 6 ) alkyl group,

R 4 represents (d8) a halo (C 1 -C 6 ) alkyl group,

A, A 2 and A 3 each represent a nitrogen atom,

A 1 represents N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group),

m represents 2, and

n represents 1.

11. The condensed heterocyclic compound according to claim 7 or a salt thereof, wherein the condensed heterocyclic compound is represented by formula (1B):

wherein

R 1 represents

(a1) a (C 1 -C 6 ) alkyl group;

(a2) a (C 3 -C 6 ) cycloalkyl group;

(a3) a (C 2 -C 6 ) alkenyl group; or

(a4) a (C 2 -C 6 ) alkynyl group,

R 2 represents

(b1) a hydrogen atom;

(b2) a (C 1 -C 6 ) alkyl group;

(b3) a (C 3 -C 6 ) cycloalkyl group; or

(b5) an amino group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c4) a (C 2 -C 6 ) alkynyl group;

(c5) a (C 3 -C 6 ) cycloalkyl group;

(c6) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c8) a halo (C 1 -C 6 ) alkyl group;

(c9) a halo (C 2 -C 6 ) alkenyl group;

(c10) a halo (C 2 -C 6 ) alkynyl group;

(c11) a phenyl group;

(c12) a phenyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group;

(c13) a phenyl (C 1 -C 6 ) alkyl group; or

(c14) a phenyl (C 1 -C 6 ) alkyl group having, on the ring, 1 to 5 substituting groups which may be the same or different and are selected from (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g) a (C 1 -C 6 ) alkoxy group, (h) a halo (C 1 -C 6 ) alkoxy group, (i) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) a (C 1 -C 6 ) alkylthio group, (k) a halo (C 1 -C 6 ) alkylthio group, (l) a (C 1 -C 6 ) alkylsulfinyl group, (m) a halo (C 1 -C 6 ) alkylsulfinyl group, (n) a (C 1 -C 6 ) alkylsulfonyl group and (o) a halo (C 1 -C 6 ) alkylsulfonyl group,

R 4 represents

(d1) a halogen atom;

(d2) a cyano group;

(d3) a nitro group;

(d4) a (C 1 -C 6 ) alkyl group;

(d5) a (C 1 -C 6 ) alkoxy group;

(d6) a (C 2 -C 6 ) alkenyloxy group;

(d7) a (C 2 -C 6 ) alkynyloxy group;

(d8) a halo (C 1 -C 6 ) alkyl group;

(d9) a halo (C 1 -C 6 ) alkoxy group;

(d10) a halo (C 2 -C 6 ) alkenyloxy group;

(d11) a halo (C 2 -C 6 ) alkynyloxy group;

(d12) a (C 1 -C 6 ) alkylthio group;

(d13) a (C 1 -C 6 ) alkylsulfinyl group;

(d14) a (C 1 -C 6 ) alkylsulfonyl group;

(d15) a halo (C 1 -C 6 ) alkylthio group;

(d16) a halo (C 1 -C 6 ) alkylsulfinyl group; or

(d17) a halo (C 1 -C 6 ) alkylsulfonyl group,

A, A 2 and A 3 each represent CH or a nitrogen atom,

A 1 represents O, S or N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group; (e2) a (C 3 -C 6 ) cycloalkyl group; (e3) a (C 2 -C 6 ) alkenyl group; or (e4) a (C 2 -C 6 ) alkynyl group),

m represents 0, 1 or 2, and

n represents 0, 1 or 21.

12. The condensed heterocyclic compound according to claim 11 or a salt thereof, wherein

R 1 represents (a1) a (C 1 -C 6 ) alkyl group,

R 2 represents

(b1) a hydrogen atom; or

(b2) a (C 1 -C 6 ) alkyl group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c11) a phenyl group; or

(c13) a phenyl (C 1 -C 6 ) alkyl group,

R 4 represents

(d8) a halo (C 1 -C 6 ) alkyl group; or

(d15) a halo (C 1 -C 6 ) alkylthio group,

A, A 2 and A 3 each represent a nitrogen atom,

A 1 represents N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group),

m represents 0, 1 or 2, and

n represents 1.

13. The condensed heterocyclic compound according to claim 11 or a salt thereof, wherein

R 1 represents (a1) a (C 1 -C 6 ) alkyl group,

R 2 represents

(b1) a hydrogen atom; or

(b2) a (C 1 -C 6 ) alkyl group,

R 3 represents

(c1) a hydrogen atom;

(c2) a (C 1 -C 6 ) alkyl group;

(c3) a (C 2 -C 6 ) alkenyl group;

(c7) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group;

(c11) a phenyl group; or

(c13) a phenyl (C 1 -C 6 ) alkyl group,

R 4 represents (d8) a halo (C 1 -C 6 ) alkyl group,

A, A 2 and A 3 each represent a nitrogen atom,

A 1 represents N—R 5 (wherein R 5 represents (e1) a (C 1 -C 6 ) alkyl group),

m represents 2, and

n represents 1.

14. An agricultural and horticultural insecticide comprising the condensed heterocyclic compound according to claim 7 or a salt thereof as an active ingredient.

15. A method for using an agricultural and horticultural insecticide, the method comprising applying an effective amount of the condensed heterocyclic compound according to claim 7 or a salt thereof to plants or soil.

16. An animal ectoparasite control agent comprising an effective amount of the condensed heterocyclic compound according to claim 7 or a salt thereof as an active ingredient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2020
From: SANO, YUSUKE; YONEMURA, IKKI; MATSUO, SOICHIRO; SUWA, AKIYUKI; FUJIE, SHUNPEI
To: NIHON NOHYAKU CO., LTD.
Reel/Frame 053708/0026 →
Priority Claims (3)
JP 2015-201937 · Oct 13, 2015 · national
JP 2016-030466 · Feb 19, 2016 · national
JP 2016-140926 · Jul 15, 2016 · national
Continuity (1)
Related Publication 20210371424A1 · Dec 2, 2021
Cited By (1)
US 12,486,272