Fused heterocyclic compound, pyrazole-ring-containing fused heterocyclic compound, agricultural composition containing thereof, and method of using the composition

Patent metadata

Field	Value
Publication number	US-11401271-B2
Application number	US-201816758053-A
Country	US
Kind code	B2
Filing date	Nov 2, 2018
Priority date	Nov 3, 2017
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

A fused tricyclic compound, an optical isomer, cis and trans isomers or an agromedically acceptable salt thereof, and insecticidal use thereof in agroforestry. A pyrazole-ring-contained fused heterocyclic compound, an agricultural composition, and a method of using the agricultural composition are also provided.

First claim

What is claimed is:

1. A fused heterocyclic compound, and an optical isomer, cis and trans isomers or an agromedically acceptable salt thereof, the fused heterocyclic compound has a structure shown in formula (I):

wherein R 11 and R 12 are each independently hydrogen, halogen, —NO 2 , —CN, —COR 17 , —CO 2 R 17 , —CONR 17 R 18 , —S(O) R 17 , —S(O) 2 R 17 , —N R 17 R 18 , —N R 17 CO R 18 , —N R 17 CON R 18 R 19 , —N R 17 CO 2 R 18 , —N R 17 S(O) 2 R 18 , alkyl, heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl or heteroaryl; wherein the alkyl, the alkenyl, the cycloalkyl, the cycloalkenyl, the aryl, the heterocyclyl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ;
R 13 is hydrogen, —COR 17 , —CO 2 R 17 , —S(O) 2 R 17 , —CONR 17 R 18 , alkyl, heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl and aryl; wherein the alkyl, the alkenyl, the cycloalkyl, the cycloalkenyl and the aryl are unsubstituted or substituted with one or more substituents R 10 ;
R 14 and R 15 are each independently hydrogen, halogen, —CN, —OH, —N R 17 R 18 , —O R 17 , —CO R 17 , —CO 2 R 17 , —CONR 17 R 18 , —N R 17 CON R 18 , —NR 17 CON R 18 R 19 , —NR 17 CO 2 R 18 , —NR 17 S(O) 2 R 18 , —S(O)R 17 , —S(O) 2 R 17 , alkyl, heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl or heteroaryl; wherein the alkyl, the alkenyl, the cycloalkyl, the cycloalkenyl, the aryl, the heterocyclyl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 , and R 14 and R 15 are not hydrogen at the same time;
Y is N or CH;
Z 1 , Z 2 , Z 3 and Z 4 are each independently C or N, under conditions that at most two of Z 1 to Z 4 are N, and a ring containing Z 1 to Z 4 is aromatic;
R 16 represents a substituent on the ring containing Z 1 to Z 4 , one or more R 16 are provided, and each R 16 is independently hydrogen, halogen, —CN, alkyl, heteroalkyl, —CO R 17 , —CO 2 R 17 , —N R 17 R 18 , —CONR 17 R 18 , —N R 17 CO R 18 , —NR 17 CON R 18 R 19 , —NR 17 CO 2 R 18 or —NR 17 S(O) 2 R 18 ;
R 17 , R 18 and R 19 are each independently hydrogen, alkyl, heteroalkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl; wherein the alkyl, the alkenyl, the cycloalkyl, the cycloalkenyl, the aryl, the heterocyclyl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ; and
R 10 is halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, substituted or unsubstituted cycloalkyl, cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl, —CN, —NH 2 , —OR′″, —NR′″R″″, —COR′″, —CO 2 R′″, —CONR′″R″″, —NR′″COR″″, —NR′″CONR′″R″″, —NR′″CO 2 R″″, —S(O) 2 R′″ or —NR′″S(O) 2 R″″, wherein R′″ and are each independently hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl or heterocyclyl.

2. The compound according to claim 1 , or the optical isomer, the cis and trans isomers or the agromedically acceptable salt of the compound, wherein;
R 11 is halogen, —CN, —COR 17 , —CONR 17 R 18 , —S(O) R 17 , —N R 17 R 18 ,—N R 17 CO R 18 , aryl, heterocyclyl or heteroaryl; wherein the aryl, the heterocyclyl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ;
R 12 is hydrogen, —COR 17 , —CONR 17 R 18 , —S(O)R 17 , —S(O) 2 R 17 , —N R 17 R 18 , —N R 17 CO R 18 , —NR 17 CONR 18 R 19 , —NR 17 CO 2 R 18 , aryl, heterocyclyl or heteroaryl; wherein the aryl, the heterocyclyl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ;
R 13 is hydrogen, —COR 17 , alkyl, heteroalkyl or alkenyl;
R 14 is halogen, —CN, —N R 17 R 18 , —O R 17 , —CO R 17 , —CO 2 R 17 , —CONR 17 R 18 , —N R 17 CO R 18 , —NR 17 CO 2 R 18 , alkyl, heteroalkyl or alkenyl; wherein the alkyl, the heteroalkyl or the alkenyl is unsubstituted or substituted with one or more substituents R 10 ; and
R 15 is hydrogen, halogen, —CN, —N R 17 R 18 ,—O R 17 , —CO R 17 , —CO 2 R 17 , —CONR 17 R 18 , —N R 17 CO R 18 , —NR 17 CO 2 R 18 , alkyl, heteroalkyl or alkenyl; wherein the alkyl, the heteroalkyl or the alkenyl is unsubstituted or substituted with one or more substituents R 10 .

3. The compound according to claim 1 , or the optical isomer, the cis and trans isomers or the agromedically acceptable salt of the compound, wherein when Z 1 , Z 2 , Z 3 and Z 4 are all C, one or more R 16 are provided, and each R 16 is independently hydrogen, halogen, alkyl, heteroalkyl, alkenyl, —S(O) R 17 , —S(O) 2 R 17 , —COR 17 , —N R 17 R 18 , —CONR 17 R 18 , —N R 17 CO R 18 or —NR 17 S(O) 2 R 18 ;
R 11 is halogen, —CN, —COR 17 , —CONR 17 R 18 , —S(O) R 17 , —N R 17 R 18 , —N R 17 CO R 18 , aryl, heterocyclyl or heteroaryl; wherein the aryl, the heterocyclyl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ;
R 12 is —CONR 17 R 18 , —S(O) R 17 , —S(O) 2 R 17 , —N R 17 R 18 , —N R 17 CO R 18 , —N R 17 CON R 18 R 19 , aryl, heterocyclyl or heteroaryl; wherein the aryl, the heterocyclyl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ;
R 13 is hydrogen, —COR 17 , alkyl or alkenyl; and
R 14 and R 15 are each independently halogen, —CN, —N R 17 R 18 , —O R 17 , —CO R 17 , —CO 2 R 17 , —CONR 17 R 18 , —N R 17 CO R 18 , —NR 17 CO 2 R 18 , alkyl, heteroalkyl and alkenyl;
wherein the alkyl, the heteroalkyl and the alkenyl is unsubstituted or substituted with one or more substituents R 10 .

4. The compound according to claim 1 , or the optical isomer, the cis and trans isomers or the agromedically acceptable salt of the compound, wherein,
R 11 is halogen, —CN, —COR 17 , —CONR 17 R 18 , —S(O) R 17 , —N R 17 R 18 or —N R 17 CO R 18 ;
R 12 is —S(O) R 17 , —S(O) 2 R 17 , —N R 17 R 18 , —N R 17 CO R 18 , aryl or heteroaryl; wherein the aryl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ;
R 13 is hydrogen, —COR 17 , alkyl or alkenyl;
R 14 and R 15 are each independently halogen, —CN, —N R 17 R 18 , —O R 17 , —CO R 17 , —CO 2 R 17 , —CONR 17 R 18 , —N R 17 CO R 18 , —NR 17 CO 2 R 18 , alkyl, heteroalkyl or alkenyl;
wherein the alkyl or the alkenyl is unsubstituted or substituted with one or more substituents R 10 ; and
Z 1 , Z 2 , Z 3 and Z 4 are all C, one or more R 16 are provided, and each R 16 is independently halogen, alkyl, heteroalkyl, —S(O) R 17 , —S(O) 2 R 17 , —COR 17 , —N R 17 R 18 , —N R 17 CO R 18 or —NR 17 S(O) 2 R 18 .

5. The compound according to claim 4 , or the optical isomer, the cis and trans isomers or the agromedically acceptable salt of the compound, wherein,
R 11 is halogen, —CN, —COR 17 or —CONR 17 R 18 ;
R 12 is —s(o)R 17 , —S(O) 2 R 17 , —NR 17 COR 18 , aryl or heteroaryl; wherein the aryl or the heteroaryl is unsubstituted or substituted with one or more substituents R 10 ;
R 13 is hydrogen, —COR 17 or alkyl; and
Z 1 , Z 2 , and Z 4 are all C, one or more R 16 are provided, and each R 16 is independently halogen, heteroalkyl, —S(O)R 17 , —NR 17 R or —NR 17 COR 18 .

6. The compound according to claim 4 , or the optical isomer, the cis and trans isomers or the agromedically acceptable salt of the compound, wherein
R 11 —CN or —COR 17 ;
R 12 is —S(O)R 17 or aryl; wherein the aryl is substituted with one or more substituents R 10 ;
R 13 is hydrogen, —COR 17 , methyl or ethyl;
R 14 and R 15 are each independently halogen, —OR 17 , —COR 17 , —CO 2 R 17 , —CONR 17 R 18 , —NR 17 COR 18 , —NR 17 CO 2 R 18 , alkyl, heteroalkyl or alkenyl; wherein the alkyl or the alkenyl is unsubstituted or substituted with one

Assignees

• Univ South China Agricult

Inventors

• Xu Hanhong
• Jiang Xunyuan
• Wei Xiaoyi
• Zhang Zhixiang
• Lin Fei
• Yao Guangkai
• Deng Chengju
• Zhao Chen
• Yang Shuai
• Zhao Weijing

Classifications

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D471/14

  Ortho-condensed systems · CPC title

• C07D487/14 Primary

  Ortho-condensed systems · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A01N47/38

  containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof · CPC title