US 12,116,370 B2
Condensed heterocyclic compound having a bridgehead nitrogen atom or salt thereof, agricultural or horticultural insecticide comprising the compound, and method for using the insecticide
Yusuke Sano, Osaka (JP); and Ikki Yonemura, Osaka (JP)
Assigned to Nihon Nohyaku Co., Ltd., Tokyo (JP)
Appl. No. 17/595,759
Filed by Nihon Nohyaku Co., Ltd., Tokyo (JP)
PCT Filed May 26, 2020, PCT No. PCT/JP2020/020643
§ 371(c)(1), (2) Date Nov. 23, 2021,
PCT Pub. No. WO2020/241606, PCT Pub. Date Dec. 3, 2020.
Claims priority of application No. 2019-098298 (JP), filed on May 27, 2019.
Prior Publication US 2022/0242869 A1, Aug. 4, 2022
Int. Cl. C07D 487/04 (2006.01); A01N 43/90 (2006.01); A01P 7/04 (2006.01)
CPC C07D 487/04 (2013.01) [A01N 43/90 (2013.01); A01P 7/04 (2021.08)] 7 Claims
 
1. A condensed heterocyclic compound which has a bridgehead nitrogen atom and is bound to a pyridine ring containing an oxime group, the compound represented by the following formula:

OG Complex Work Unit Chemistry
wherein
R1 represents
(a1) a hydrogen atom;
(a2) a (C1-C6) alkyl group;
(a3) a (C3-C6) cycloalkyl group; or
(a4) a halo (C1-C6) alkyl group,
R2 represents
(b1) a hydrogen atom;
(b2) a (C1-C6) alkyl group;
(b3) a halo (C1-C6) alkyl group;
(b4) a (C3-C6) cycloalkyl group; or
(b5) a halo (C3-C6) cycloalkyl group,
R3 represents
(c1) a hydrogen atom;
(c2) a (C1-C6) alkyl group;
(c3) a halo (C1-C6) alkyl group;
(c4) a (C3-C6) cycloalkyl group;
(c5) a (C3-C6) cycloalkyl (C1-C6) alkyl group;
(c6) a (C1-C6) alkylthio (C1-C6) alkyl group;
(c7) a (C1-C6) alkylsulfinyl (C1-C6) alkyl group; or
(c8) a (C1-C6) alkylsulfonyl (C1-C6) alkyl group,
R4 represents
(d1) a hydrogen atom;
(d2) a halogen atom;
(d3) a cyano group;
(d4) a (C1-C6) alkyl group;
(d5) a (C2-C6) alkenyl group;
(d6) a (C3-C6) cycloalkyl group;
(d7) a (C3-C6) cycloalkyl (C2-C6) alkynyl group;
(d8) a (C1-C6) alkoxy group;
(d9) a (C1-C6) alkylthio group;
(d10) an R6 (R7) N group wherein R6 and R7 may be the same or different and each represent a hydrogen atom, a (C1-C6) alkyl group, a halo (C1-C6) alkyl group, a (C1-C6) alkoxycarbonyl group, a (C1-C6) alkylcarbonyl group, or a (C3-C6) cycloalkylcarbonyl group;
(d11) an NR6CON (R6) R7 group wherein R6 and R7 are the same as above;
(d12) an aryl group;
(d13) an aryl group having, on the ring, 1 to 4 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (l) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group;
(d14) a heterocyclic group; or
(d15) a heterocyclic group having, on the ring, 1 to 3 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 (C1-C6) alkyl group, (e) a halo (C1-C6) alkyl group, (f) a (C1-C6) alkoxy group, (g) a halo (C1-C6) alkoxy group, (h) a (C1-C6) alkylthio group, (i) a halo (C1-C6) alkylthio group, (j) a (C1-C6) alkylsulfinyl group, (k) a halo (C1-C6) alkylsulfinyl group, (l) a (C1-C6) alkylsulfonyl group, and (m) a halo (C1-C6) alkylsulfonyl group, and
A represents a nitrogen atom or C—R5 wherein R5 represents (e1) a hydrogen atom, (e2) a (C1-C6) alkyl group, or (e3) a halo (C1-C6) alkyl group, or
a salt thereof.