US 11,787,809 B2
Oxime group-containing condensed heterocyclic compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
Yusuke Sano, Osaka (JP); Ikki Yonemura, Osaka (JP); Soichiro Matsuo, Osaka (JP); Akiyuki Suwa, Osaka (JP); and Shunpei Fujie, Osaka (JP)
Assigned to NIHON NOHYAKU CO., LTD., Tokyo (JP)
Appl. No. 16/967,199
Filed by NIHON NOHYAKU CO., LTD., Tokyo (JP)
PCT Filed Oct. 12, 2016, PCT No. PCT/JP2016/080274
§ 371(c)(1), (2) Date Aug. 4, 2020,
PCT Pub. No. WO2017/065183, PCT Pub. Date Apr. 20, 2017.
Claims priority of application No. 2015-201937 (JP), filed on Oct. 13, 2015; application No. 2016-030466 (JP), filed on Feb. 19, 2016; and application No. 2016-140926 (JP), filed on Jul. 15, 2016.
Prior Publication US 2021/0371424 A1, Dec. 2, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 487/04 (2006.01); A01N 43/40 (2006.01); A01N 43/76 (2006.01); A01N 43/90 (2006.01); C07D 213/81 (2006.01); C07D 405/04 (2006.01); C07D 413/04 (2006.01); C07D 413/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 487/04 (2013.01) [A01N 43/40 (2013.01); A01N 43/76 (2013.01); A01N 43/90 (2013.01); C07D 213/81 (2013.01); C07D 405/04 (2013.01); C07D 413/04 (2013.01); C07D 413/14 (2013.01); C07D 471/04 (2013.01)] 16 Claims
 
1. A condensed heterocyclic compound represented by formula (1):

OG Complex Work Unit Chemistry
wherein
R1 represents
(a1) a (C1-C6) alkyl group;
(a2) a (C3-C6) cycloalkyl group;
(a3) a (C2-C6) alkenyl group; or
(a4) a (C2-C6) alkynyl group,
R2 represents
(b1) a hydrogen atom;
(b2) a (C1-C6) alkyl group;
(b3) a (C3-C6) cycloalkyl group;
(b4) a halo (C1-C6) alkyl group;
(b5) an amino group;
(b6) a cyano group;
(b7) a (C1-C6) alkoxycarbonyl group;
(b8) an aminocarbonyl group;
(b9) a mono-(C1-C6) alkylaminocarbonyl group; or
(b10) a di-(C1-C6) alkylaminocarbonyl group,
R3 represents
(c1) a hydrogen atom;
(c2) a (C1-C6) alkyl group;
(c3) a (C2-C6) alkenyl group;
(c4) a (C2-C6) alkynyl group;
(c5) a (C3-C6) cycloalkyl group;
(c6) a (C3-C6) cycloalkyl (C1-C6) alkyl group;
(c7) a (C1-C6) alkoxy (C1-C6) alkyl group;
(c8) a halo (C1-C6) alkyl group;
(c9) a halo (C2-C6) alkenyl group;
(c10) a halo (C2-C6) 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 (C1-C6) alkyl group, (f) a halo (C1-C6) alkyl group, (g) a (C1-C6) alkoxy group, (h) a halo (C1-C6) alkoxy group, (i) a (C3-C6) cycloalkyl (C1-C6) alkoxy group, (j) a (C1-C6) alkylthio group, (k) a halo (C1-C6) alkylthio group, (l) a (C1-C6) alkylsulfinyl group, (m) a halo (C1-C6) alkylsulfinyl group, (n) a (C1-C6) alkylsulfonyl group and (o) a halo (C1-C6) alkylsulfonyl group;
(c13) a phenyl (C1-C6) alkyl group;
(c14) a phenyl (C1-C6) 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 (C1-C6) alkyl group, (f) a halo (C1-C6) alkyl group, (g) a (C1-C6) alkoxy group, (h) a halo (C1-C6) alkoxy group, (i) a (C3-C6) cycloalkyl (C1-C6) alkoxy group, (j) a (C1-C6) alkylthio group, (k) a halo (C1-C6) alkylthio group, (l) a (C1-C6) alkylsulfinyl group, (m) a halo (C1-C6) alkylsulfinyl group, (n) a (C1-C6) alkylsulfonyl group and (o) a halo (C1-C6) alkylsulfonyl group;
(c15) a (C1-C6) alkylcarbonyl group;
(c16) a (C3-C6) cycloalkylcarbonyl group;
(c17) a cyanoalkyl group;
(c18) a (C1-C6) alkylthio (C1-C6) alkyl group;
(c19) a (C1-C6) alkylsulfinyl (C1-C6) alkyl group;
(c20) a (C1-C6) alkylsulfonyl (C1-C6) alkyl group;
(c21) a halo (C1-C6) alkylthio (C1-C6) alkyl group;
(c22) a halo (C1-C6) alkylsulfinyl (C1-C6) alkyl group; or
(c23) a halo (C1-C6) alkylsulfonyl (C1-C6) alkyl group,
R4 represents
(d1) a halogen atom;
(d2) a cyano group;
(d3) a nitro group;
(d4) a (C1-C6) alkyl group;
(d5) a (C1-C6) alkoxy group;
(d6) a (C2-C6) alkenyloxy group;
(d7) a (C2-C6) alkynyloxy group;
(d8) a halo (C1-C6) alkyl group;
(d9) a halo (C1-C6) alkoxy group;
(d10) a halo (C2-C6) alkenyloxy group;
(d11) a halo (C2-C6) alkynyloxy group;
(d12) a (C1-C6) alkylthio group;
(d13) a (C1-C6) alkylsulfinyl group;
(d14) a (C1-C6) alkylsulfonyl group;
(d15) a halo (C1-C6) alkylthio group;
(d16) a halo (C1-C6) alkylsulfinyl group; or
(d17) a halo (C1-C6) alkylsulfonyl group,
A, A2 and A3 each represent CH or a nitrogen atom,
A1 represents O, S or N—R5 (wherein R5 represents (e1) a (C1-C6) alkyl group; (e2) a (C3-C6) cycloalkyl group; (e3) a (C2-C6) alkenyl group; or (e4) a (C2-C6) alkynyl group),
m represents 0, 1 or 2, and
n represents 0, 1 or 2, or
a salt thereof.