US 12,240,843 B2
Substituted 1,2,4-triazolo[4,3-a]pyridine derivative and preparation method, herbicidal composition and application thereof
Lei Lian, Qingdao (CN); Xuegang Peng, Qingdao (CN); Rongbao Hua, Qingdao (CN); De Zhao, Qingdao (CN); and Qi Cui, Qingdao (CN)
Assigned to Qingdao Kingagroot Chemical Compound Co., Ltd., Qingdao (CN)
Appl. No. 17/414,501
Filed by Qingdao Kingagroot Chemical Compound Co., Ltd., Qingdao (CN)
PCT Filed Jul. 17, 2020, PCT No. PCT/CN2020/102660
§ 371(c)(1), (2) Date Jun. 16, 2021,
PCT Pub. No. WO2021/008607, PCT Pub. Date Jan. 21, 2021.
Claims priority of application No. 201910650905.6 (CN), filed on Jul. 18, 2019.
Prior Publication US 2023/0075221 A1, Mar. 9, 2023
Int. Cl. C07D 471/04 (2006.01); A01N 43/90 (2006.01)
CPC C07D 471/04 (2013.01) [A01N 43/90 (2013.01)] 9 Claims
 
1. A substituted 1,2,4-triazolo[4,3-a]pyridine derivative of Formula I:

OG Complex Work Unit Chemistry
Q represents

OG Complex Work Unit Chemistry
R11 represents C1-C6 alkyl;
R12 represents hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl;
R13 represents hydrogen, sodium ion or —(C═O)R64;
R21 and R22 each independently represent hydrogen or C3-C6 cycloalkyl;
R41, R41′, R42, R42′, R43 and R43′ each independently represent hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl, or two of R41, R41′, R42, R42′, R43 and R43′ that are on different carbon atoms connect to form (CH2)2;
R44 is selected from —ONa;
R51, R51′, R52, R52′, R53 and R53′ each independently represent hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl, or two of R51, R51′, R52, R52′, R53 and R53′ that are on different carbon atoms connect to form CH2 or (CH2)2;
R64 represents aryl or heterocyclyl;
X represents fluorine, chlorine, bromine, iodine, C3-C6 cycloalkyl, or C1-C6 alkylthio;
R1 and R2 each independently represent C1-C6 alkyl, or —NR1R2 represents butyrolactam group;
Y represents hydrogen; fluorine; chlorine; bromine; iodine; formyl; cyano-C1-C3 alkyl; a C1-C10 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, each of which contains or does not contain a fluorine or chlorine; —OR3; —COR4; —SR3; —SOR4; —SO2R4; —(C1-C3 alkyl)-OR3; —(C1-C6 alkyl)-OCOR4; —(C1-C3 alkyl)-SR3; —(C1-C3 alkyl)-SOR4; —(C1-C3 alkyl)-SO2R4; an amino, amino-C1-C3 alkyl or aminoacyl, each of which is unsubstituted or substituted with 1 to 2 groups selected from C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl and C1-C6 alkylacyl; a C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl or C3-C6 cycloalkenyl, each of which is unsubstituted or substituted with 1 to 2 groups selected from C1-C6 alkyl, cyano and fluorine; aryl; heterocyclyl; aryl-C1-C3 alkyl or heterocyclyl-C1-C3 alkyl;
R3 each independently represents hydrogen, sodium ion, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl;
R4 each independently represents C1-C6alkyl;
Z represents hydrogen, fluorine or chlorine;
the aryl or heterocyclyl is substituted or unsubstituted, respectively, and said substituted refers to being substituted with 1 to 2 groups selected from fluorine, chlorine, cyano, C1-C6 alkyl and phenyl;
the aryl is selected from phenyl and naphthyl; the heterocyclyl is selected from

OG Complex Work Unit Chemistry