IP Library › Granted Patent US 12,389,911
Granted Patent B2
US 12,389,911 · App. 17/780,853 · Granted Aug 19, 2025

Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent containing said compound, and method for using same

Inventors: Hirokazu Fujihara (Kawachinagano, JP); Kazuki Fujii (Kawachinagano, JP); Shunsuke Fuchi (Kawachinagano, JP); Ryosuke Tanaka (Kawachinagano, JP); Kenta Akimoto (Kawachinagano, JP)
Assignee: NIHON NOHYAKU CO., LTD.
A01N43/52A01P7/02A01P7/04C07D403/04
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Quick Facts
Patent No.
US 12,389,911
App. No.
17/780,853
Granted
Aug 19, 2025
Kind
B2
Abstract

The present invention provides a benzimidazole compound represented by the general formula (1) wherein R is an alkyl group or the like, Y 1 , Y 2 , Y 3 , and Y 4 are a hydrogen atom or the like, Q is a 5-membered heterocyclic group optionally having a substituent such as a substituted imidazole bound at a nitrogen atom and a substituted pyrazole bound at a nitrogen atom, or a salt thereof, an agricultural and horticultural insecticidal and acaricidal agent having the compound or a salt thereof as an active ingredient, and a method for using the same.

Claims (223)

1. A benzimidazole compound represented by a general formula (1)

wherein R is

a (C 1 -C 6 ) alkyl group;

a (C 3 -C 6 ) cycloalkyl group;

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

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

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

a (C 2 -C 6 ) alkynyl group,

Y 1 , Y 2 , Y 3 and Y 4 , the same or different, are

a hydrogen atom;

a halogen atom;

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

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

Q is selected from the following nitrogen-containing 5-membered heterocyclic groups,

wherein X 1 and X 4 , the same or different, are

a hydrogen atom; or

a (C 1 -C 6 ) alkyl group,

X 2 is

a hydrogen atom;

a halogen atom;

a cyano group;

a (C 1 -C 12 ) alkyl group;

a (C 3 -C 6 ) cycloalkyl group;

a (C 2 -C 12 ) alkenyl group;

a (C 2 -C 12 ) alkynyl group;

a (C 1 -C 6 ) alkoxy group;

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

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

a (C 1 -C 6 ) alkylthio group;

a (C 1 -C 6 ) alkylsulfinyl group;

a (C 1 -C 6 ) alkylsulfonyl group;

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

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

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

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

a (C 3 -C 6 ) cycloalkyl (C 2 -C 6 ) alkynyl group;

a (C 1 -C 6 ) alkylcarbonyl group;

a (C 1 -C 6 ) alkoxycarbonyl group;

a (C 2 -C 6 ) alkynyloxycarbonyl group;

a (C 1 -C 6 ) alkylthiocarbonyl group;

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

a (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

an aryloxy (C 1 -C 6 ) alkyl group;

an aryloxy (C 1 -C 6 ) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryloxycarbonyl group;

an aryloxycarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an arylcarbonyl group;

an arylcarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 1 -C 6 ) alkyl group;

an aryl (C 1 -C 6 ) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 2 -C 6 ) alkynyl group;

an aryl (C 2 -C 6 ) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

a R 1 R 2 N group, wherein R 1 and R 2 , the same or different, are (aa) a hydrogen atom, (ab) a (C 1 -C 6 ) alkyl group, (ac) a (C 1 -C 6 ) alkoxy group, (ad) a (C 1 -C 6 ) alkoxycarbonyl group, (ae) a (C 1 -C 6 ) alkylsulfonyl group, (af) a halo (C 1 -C 6 ) alkylsulfonyl group, (ag) an aryl group, (ah) a (C 3 -C 6 ) cycloalkyl group, (ai) a halo (C 1 -C 6 ) alkyl group, or (aj) an aryl (C 1 -C 6 ) alkyl group;

a R 1 R 2 N carbonyl group, wherein R 1 and R 2 have the same meaning as above;

a R 1 R 2 N sulfonyl group, wherein R 1 and R 2 have the same meaning as above;

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

a halo (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

a (C 3 -C 12 ) cycloalkyl (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

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

a heteroaryl (C 2 -C 6 ) alkynyl group having the same or different one to four substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

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

a (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

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

a (C 1 -C 6 ) alkylcarbonyloxy (C 2 -C 6 ) alkynyl group;

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

a halo (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

an aryloxy (C 2 -C 6 ) alkynyl group;

an aryloxy (C 2 -C 6 ) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

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

a (C 1 -C 6 ) alkylaminocarbonyl (C 2 -C 6 ) alkenyl group;

a halo (C 1 -C 6 ) alkylaminocarbonyl (C 2 -C 6 ) alkenyl group;

an aryl (C 1 -C 6 ) alkylthio group; or an aryl (C 1 -C 6 ) alkylthio group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group,

X 3 is

a hydrogen atom;

a halogen atom;

a (C 1 -C 6 ) alkyl group;

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

a (C 1 -C 6 ) alkoxy group;

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

a (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

a (C 1 -C 6 ) alkylthio group;

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

a (C 1 -C 6 ) alkoxycarbonyl group;

a (C 2 -C 6 ) alkynyloxycarbonyl group;

an aryl (C 1 -C 6 ) alkyl group;

an aryl (C 1 -C 6 ) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an arylsulfonyl group;

an arylsulfonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryloxycarbonyl group;

an aryloxycarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 1 -C 6 ) alkoxy group;

an aryl (C 1 -C 6 ) alkoxy group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

a (C 3 -C 6 ) cycloalkyl group;

a (C 3 -C 6 ) cycloalkyl (C 2 -C 6 ) alkenyl group;

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

a (C 2 -C 6 ) alkenyl group;

an aryl (C 2 -C 6 ) alkynyl group;

an aryl (C 2 -C 6 ) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

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

a (C 2 -C 6 ) alkynyloxy group;

a cyano group;

a (C 2 -C 6 ) alkynyl group;

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

a (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

a halo (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

a R 1 R 2 N carbonyl group, wherein R 1 and R 2 have the same meaning as above;

a R 1 R 2 N carbonyl (C 1 -C 6 ) alkoxy group, wherein R 1 and R 2 have the same meaning as above;

a R 1 R 2 N carbonyl halo (C 1 -C 6 ) alkoxy group, wherein R 1 and R 2 have the same meaning as above; or

X 2 and X 3 may be combined to form a 5- to 8-membered aliphatic ring together with the carbon atoms to which they are bound, and the aliphatic ring may have one to five substituents selected from a (C 1 -C 6 ) alkyl group and an oxo group, wherein the moiety at which the • mark is shown binds to benzimidazole;

or a salt thereof.

2. The benzimidazole compound according to claim 1 ,

wherein

R is

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

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

Y 1 , Y 2 , Y 3 and Y 4 , the same or different, are

a hydrogen atom;

a halogen atom;

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

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

X 1 and X 4 , the same or different, are

a hydrogen atom; or

a (C 1 -C 6 ) alkyl group,

X 2 is

a hydrogen atom;

a halogen atom;

a cyano group;

a (C 1 -C 12 ) alkyl group;

a (C 3 -C 6 ) cycloalkyl group;

a (C 2 -C 12 ) alkenyl group;

a (C 2 -C 12 ) alkynyl group;

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

a (C 1 -C 6 ) alkylthio group;

a (C 1 -C 6 ) alkylsulfinyl group;

a (C 1 -C 6 ) alkylsulfonyl group;

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

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

a (C 3 -C 6 ) cycloalkyl (C 2 -C 6 ) alkynyl group;

a (C 1 -C 6 ) alkylcarbonyl group;

a (C 1 -C 6 ) alkoxycarbonyl group;

a (C 2 -C 6 ) alkynyloxycarbonyl group;

a (C 1 -C 6 ) alkylthiocarbonyl group;

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

a (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

an aryloxy (C 1 -C 6 ) alkyl group;

an aryloxy (C 1 -C 6 ) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryloxycarbonyl group;

an aryloxycarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an arylcarbonyl group;

an arylcarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 1 -C 6 ) alkyl group;

an aryl (C 1 -C 6 ) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 2 -C 6 ) alkynyl group;

an aryl (C 2 -C 6 ) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

a R 1 R 2 N carbonyl group, wherein R 1 and R 2 have the same meaning as above;

a R 1 R 2 N sulfonyl group, wherein R 1 and R 2 have the same meaning as above;

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

a halo (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

an aryl (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

a (C 3 -C 12 ) cycloalkyl (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

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

a heteroaryl (C 2 -C 6 ) alkynyl group having the same or different one to four substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

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

a (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

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

a (C 1 -C 6 ) alkylcarbonyloxy (C 2 -C 6 ) alkynyl group;

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

a halo (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

an aryloxy (C 2 -C 6 ) alkynyl group;

an aryloxy (C 2 -C 6 ) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

a (C 1 -C 6 ) alkylaminocarbonyl (C 2 -C 6 ) alkenyl group;

a halo (C 1 -C 6 ) alkylaminocarbonyl (C 2 -C 6 ) alkenyl group;

an aryl (C 1 -C 6 ) alkylthio group; or

an aryl (C 1 -C 6 ) alkylthio group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group,

X 3 is

a hydrogen atom;

a halogen atom;

a (C 1 -C 6 ) alkyl group;

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

a (C 1 -C 6 ) alkoxy group;

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

a (C 1 -C 6 ) alkoxycarbonyl (C 2 -C 6 ) alkenyl group;

a (C 1 -C 6 ) alkylthio group;

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

a (C 1 -C 6 ) alkoxycarbonyl group;

an aryl (C 1 -C 6 ) alkyl group;

an aryl (C 1 -C 6 ) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an arylsulfonyl group;

an arylsulfonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

an aryl (C 1 -C 6 ) alkoxy group;

an aryl (C 1 -C 6 ) alkoxy group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

a (C 3 -C 6 ) cycloalkyl group;

a (C 3 -C 6 ) cycloalkyl (C 2 -C 6 ) alkenyl group;

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

a (C 2 -C 6 ) alkenyl group;

an aryl (C 2 -C 6 ) alkynyl group;

an aryl (C 2 -C 6 ) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) a (C 1 -C 6 ) alkoxy group, (e) a halo (C 1 -C 6 ) alkoxy group, (f) a (C 1 -C 6 ) alkylthio group, (g) a halo (C 1 -C 6 ) alkylthio group, (h) a (C 1 -C 6 ) alkylsulfinyl group, (i) a halo (C 1 -C 6 ) alkylsulfinyl group, (j) a (C 1 -C 6 ) alkylsulfonyl group, and (k) a halo (C 1 -C 6 ) alkylsulfonyl group;

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

a (C 2 -C 6 ) alkynyloxy group;

a cyano group;

a (C 2 -C 6 ) alkynyl group;

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

a (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

a halo (C 1 -C 6 ) alkoxy (C 2 -C 6 ) alkynyl group;

a R 1 R 2 N carbonyl group, wherein R 1 and R 2 have the same meaning as above;

a R 1 R 2 N carbonyl (C 1 -C 6 ) alkoxy group, wherein R 1 and R 2 have the same meaning as above;

a R 1 R 2 N carbonyl halo (C 1 -C 6 ) alkoxy group, wherein R 1 and R 2 have the same meaning as above; or

X 2 and X 3 may be combined to form a 5- to 8-membered aliphatic ring together with the carbon atoms to which they are bound, and the aliphatic ring may have one to five substituents selected from a (C 1 -C 6 ) alkyl group and an oxo group;

or a salt thereof.

3. The benzimidazole compound or a salt thereof according to claim 1 , wherein Q is Q-2, Q-3, or Q-4.

4. An agricultural and horticultural insecticidal and acaricidal agent, comprising the benzimidazole compound or a salt thereof according to claim 1 as an active ingredient.

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

6. An ectoparasite control agent for animals, comprising the benzimidazole compound or a salt thereof according to claim 1 as an active ingredient.

7. An endoparasite control agent for animals, comprising the benzimidazole compound or a salt thereof according to claim 1 as an active ingredient.

8. A method for controlling ectoparasites, comprising orally or parenterally administering, to an animal in need thereof, an effective amount of the benzimidazole compound or a salt thereof according to claim 1 as an active ingredient.

9. A method for controlling endoparasites, comprising orally or parenterally administering, to an animal in need thereof, an effective amount of the benzimidazole compound or a salt thereof according to claim 1 as an active ingredient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 31, 2022
From: FUJIHARA, HIROKAZU; FUJII, KAZUKI; FUCHI, SHUNSUKE; TANAKA, RYOSUKE; AKIMOTO, KENTA
To: NIHON NOHYAKU CO., LTD.
Reel/Frame 060060/0196 →
Priority Claims (1)
JP 2019-215007 · Nov 28, 2019 · national
Continuity (1)
Related Publication 20230056277A1 · Feb 23, 2023
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