US 12,389,911 B2
Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent containing said compound, and method for using same
Hirokazu Fujihara, Kawachinagano (JP); Kazuki Fujii, Kawachinagano (JP); Shunsuke Fuchi, Kawachinagano (JP); Ryosuke Tanaka, Kawachinagano (JP); and Kenta Akimoto, Kawachinagano (JP)
Assigned to NIHON NOHYAKU CO., LTD., Tokyo (JP)
Appl. No. 17/780,853
Filed by NIHON NOHYAKU CO., LTD., Tokyo (JP)
PCT Filed Nov. 27, 2020, PCT No. PCT/JP2020/044267
§ 371(c)(1), (2) Date May 27, 2022,
PCT Pub. No. WO2021/107110, PCT Pub. Date Jun. 3, 2021.
Claims priority of application No. 2019-215007 (JP), filed on Nov. 28, 2019.
Prior Publication US 2023/0056277 A1, Feb. 23, 2023
Int. Cl. A01N 43/52 (2006.01); A01P 7/02 (2006.01); A01P 7/04 (2006.01); C07D 403/04 (2006.01)
CPC A01N 43/52 (2013.01) [A01P 7/02 (2021.08); A01P 7/04 (2021.08); C07D 403/04 (2013.01)] 9 Claims
 
1. A benzimidazole compound represented by a general formula (1)

OG Complex Work Unit Chemistry
wherein R is
a (C1-C6) alkyl group;
a (C3-C6) cycloalkyl group;
a (C3-C6) cycloalkyl (C1-C6) alkyl group;
a halo (C1-C6) alkyl group;
a (C2-C6) alkenyl group; or
a (C2-C6) alkynyl group,
Y1, Y2, Y3 and Y4, the same or different, are
a hydrogen atom;
a halogen atom;
a (C1-C6) alkyl group; or
a halo (C1-C6) alkyl group,
Q is selected from the following nitrogen-containing 5-membered heterocyclic groups,

OG Complex Work Unit Chemistry
wherein X1 and X4, the same or different, are
a hydrogen atom; or
a (C1-C6) alkyl group,
X2 is
a hydrogen atom;
a halogen atom;
a cyano group;
a (C1-C12) alkyl group;
a (C3-C6) cycloalkyl group;
a (C2-C12) alkenyl group;
a (C2-C12) alkynyl group;
a (C1-C6) alkoxy group;
a halo (C1-C6) alkyl group;
a halo (C1-C6) alkoxy group;
a (C1-C6) alkylthio group;
a (C1-C6) alkylsulfinyl group;
a (C1-C6) alkylsulfonyl group;
a halo (C1-C6) alkylthio group;
a halo (C1-C6) alkylsulfinyl group;
a halo (C1-C6) alkylsulfonyl group;
a halo (C1-C6) alkoxy (C1-C6) alkyl group;
a (C3-C6) cycloalkyl (C2-C6) alkynyl group;
a (C1-C6) alkylcarbonyl group;
a (C1-C6) alkoxycarbonyl group;
a (C2-C6) alkynyloxycarbonyl group;
a (C1-C6) alkylthiocarbonyl group;
a (C1-C6) alkoxycarbonyl (C1-C6) alkyl group;
a (C1-C6) alkoxycarbonyl (C2-C6) alkenyl group;
an aryloxy (C1-C6) alkyl group;
an aryloxy (C1-C6) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) 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 (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) 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 (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
an aryl (C1-C6) alkyl group;
an aryl (C1-C6) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
an aryl (C1-C6) alkoxycarbonyl group;
an aryl (C1-C6) alkoxycarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
an aryl (C2-C6) alkynyl group;
an aryl (C2-C6) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
a R1R2N group, wherein R1 and R2, the same or different, are (aa) a hydrogen atom, (ab) a (C1-C6) alkyl group, (ac) a (C1-C6) alkoxy group, (ad) a (C1-C6) alkoxycarbonyl group, (ae) a (C1-C6) alkylsulfonyl group, (af) a halo (C1-C6) alkylsulfonyl group, (ag) an aryl group, (ah) a (C3-C6) cycloalkyl group, (ai) a halo (C1-C6) alkyl group, or (aj) an aryl (C1-C6) alkyl group;
a R1R2N carbonyl group, wherein R1 and R2 have the same meaning as above;
a R1R2N sulfonyl group, wherein R1 and R2 have the same meaning as above;
a halo (C1-C6) alkoxycarbonyl group;
a halo (C1-C6) alkoxycarbonyl (C2-C6) alkenyl group;
an aryl (C1-C6) alkoxycarbonyl (C2-C6) alkenyl group;
an aryl (C1-C6) alkoxycarbonyl (C2-C6) alkenyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
a (C3-C12) cycloalkyl (C1-C6) alkoxycarbonyl (C2-C6) alkenyl group;
a heteroaryl (C2-C6) alkynyl group;
a heteroaryl (C2-C6) alkynyl group having the same or different one to four substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
a (C3-C6) cycloalkyl (C1-C6) alkyl group;
a (C1-C6) alkoxy (C2-C6) alkynyl group;
a (C1-C6) alkoxy (C1-C6) alkyl group;
a (C1-C6) alkylcarbonyloxy (C2-C6) alkynyl group;
a (C1-C6) alkylcarbonyloxy (C1-C6) alkyl group;
a halo (C1-C6) alkoxy (C2-C6) alkynyl group;
an aryloxy (C2-C6) alkynyl group;
an aryloxy (C2-C6) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
a 1-(C1-C6) alkoxyimino (C1-C6) alkyl group;
a (C1-C6) alkylaminocarbonyl (C2-C6) alkenyl group;
a halo (C1-C6) alkylaminocarbonyl (C2-C6) alkenyl group;
an aryl (C1-C6) alkylthio group; or an aryl (C1-C6) alkylthio group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group,
X3 is
a hydrogen atom;
a halogen atom;
a (C1-C6) alkyl group;
a halo (C1-C6) alkyl group;
a (C1-C6) alkoxy group;
a halo (C1-C6) alkoxy group;
a (C1-C6) alkoxycarbonyl (C2-C6) alkenyl group;
a (C1-C6) alkylthio group;
a (C1-C6) alkoxycarbonyl (C1-C6) alkoxy group;
a (C1-C6) alkoxycarbonyl group;
a (C2-C6) alkynyloxycarbonyl group;
an aryl (C1-C6) alkyl group;
an aryl (C1-C6) alkyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) 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 (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) 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 (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
an aryl (C1-C6) alkoxycarbonyl group;
an aryl (C1-C6) alkoxycarbonyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
an aryl (C1-C6) alkoxy group;
an aryl (C1-C6) alkoxy group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
a (C3-C6) cycloalkyl group;
a (C3-C6) cycloalkyl (C2-C6) alkenyl group;
a (C3-C6) cycloalkyl (C1-C6) alkyl group;
a (C2-C6) alkenyl group;
an aryl (C2-C6) alkynyl group;
an aryl (C2-C6) alkynyl group having the same or different one to five substituents selected from (a) a halogen atom, (b) a (C1-C6) alkyl group, (c) a halo (C1-C6) alkyl group, (d) a (C1-C6) alkoxy group, (e) a halo (C1-C6) alkoxy group, (f) a (C1-C6) alkylthio group, (g) a halo (C1-C6) alkylthio group, (h) a (C1-C6) alkylsulfinyl group, (i) a halo (C1-C6) alkylsulfinyl group, (j) a (C1-C6) alkylsulfonyl group, and (k) a halo (C1-C6) alkylsulfonyl group;
a (C1-C6) alkoxy (C1-C6) alkyl group;
a (C2-C6) alkynyloxy group;
a cyano group;
a (C2-C6) alkynyl group;
a (C1-C6) alkoxycarbonyl (C1-C6) alkyl group;
a (C1-C6) alkoxy (C2-C6) alkynyl group;
a halo (C1-C6) alkoxy (C2-C6) alkynyl group;
a R1R2N carbonyl group, wherein R1 and R2 have the same meaning as above;
a R1R2N carbonyl (C1-C6) alkoxy group, wherein R1 and R2 have the same meaning as above;
a R1R2N carbonyl halo (C1-C6) alkoxy group, wherein R1 and R2 have the same meaning as above; or
X2 and X3 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 (C1-C6) alkyl group and an oxo group, wherein the moiety at which the • mark is shown binds to benzimidazole;
or a salt thereof.