Search

WO-2026092464-A1 - SUBSTITUTED HETEROCYCLIC COMPOUND AND PREPARATION METHOD THEREFOR, AND INSECTICIDAL COMPOSITION THEREOF AND USE THEREOF

WO2026092464A1WO 2026092464 A1WO2026092464 A1WO 2026092464A1WO-2026092464-A1

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to a substituted heterocyclic compound and a preparation method therefor, and an insecticidal composition thereof and the use thereof. The compound is as represented by general formula I, wherein Q represents Q-1 and Q-2; X represents an alkyl, haloalkyl, etc.; Y represents O or N-Y 1 ; R 4 and R 5 each independently represents a hydrogen, halogen, alkyl, etc.; and Y 1 and R 6 each independently represents a hydrogen, alkyl, haloalkyl, etc. The compound exhibits a great control effect on Spodoptera frugiperda, Spodoptera litura, Mythimna separata, Nilaparvata, etc.

Inventors

  • LIAN, LEI
  • PENG, Xuegang
  • GUO, Xiang
  • ZHAO, De

Assignees

  • 青岛清原化合物有限公司

Dates

Publication Date
20260507
Application Date
20251028
Priority Date
20241028

Claims (13)

  1. A substituted heterocyclic compound or its salt or oxide as shown in general formula I: Where Q represents Q3 represents N or CR 11 , Q4 represents N or CR 9 , and Q5 represents N or CR 10 . Q 8 represents N or CR 19 ; R4 , R5 , R7 , R8 , R9 , R10 , R11 , R16 , R17 , R18 , R19 , and R20 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, cycloalkenyl, -SF5 , -OR51 , -O-alkylene- OR51 , -SR51 , -O-alkylene- SR51 , -SOR51 , -( SO2 ) R51 , and -O( SO2 ) R51 , respectively. -N(R 51 ) 2 , -O(CO)R 51 , -O(CS)OR 51 , -O(CS)SR 51 , -N(R 51 )(COR 51 ), -N(R 51 )(COOR 51 ), -N(SO 2 R 51 ) 2 , -(CO)OR 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, trialkylsilyl, -OR 51 , -SR 51 , -SOR 51 , -(SO 2 )R 51 , -N(R 51 ) 2 , -O(CO)R 51 , -O(CO)OR 51 It is substituted by at least one of the groups in -(CO)R 51 or -(CO)N(R 51 ) 2 ; X represents alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cycloalkyl, cycloalkylalkyl, -N(R 51 ) 2 , aryl, heterocyclic, arylalkyl or heterocyclic alkyl; or -N(R 51 ) 2 together to form an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position; Y represents O or NY 1 ; Y1 and R6 independently represent hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cyano, -N( R51 ) 2 , -(CO) R51 , -(CO) OR51 , -(CO)N( R51 ) 2 , -OR51 , -alkylene- OR51 , -( SO2 ) R51 , cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl; R 51 is independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl; The aforementioned “cycloalkyl”, “heterocyclic”, “aryl” or “cycloalkenyl” may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R) 2 , -(CS)N(R) 2 , -(SO)R or -( SO2 )R; R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted with at least one group selected from halogen, hydroxyl, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.
  2. A substituted heterocyclic compound or its salt or oxide according to claim 1, characterized in that, R4 , R5 , R7 , R8 , R9 , R10 , R11 , R16 , R17 , R18 , R19 , and R20 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, C3-C8 cycloalkenyl, -SF5 , -OR51 , -O-(C1-C8 alkylene) -OR51 , -SR51 , -O-(C1-C8 alkylene) -SR51 , -SOR51 , -( SO2 ) R51 , and -O( SO2 ) R51 , respectively. -N(R 51 ) 2 , -O(CO )R 51 , -O(CS)OR 51 , -O(CS)SR 51 , -N(R 51 )(COR 51 ), -N(R 51 )(COOR 51 ), -N(SO 2 R 51 ) 2 , -(CO)OR 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, triC1-C8 alkylsilyl, -OR 51 , -SR 51 , -SOR 51 , -(SO 2 )R 51 , -N(R 51 ) 2. Replaced by at least one of the groups selected from -O(CO)R 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; X represents C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, -N(R 51 ) 2 , aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl; or -N(R 51 ) 2 together to form Among them, the It is either unsubstituted or substituted with at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl; Y1 and R6 independently represent hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, cyano, -N( R51 ) 2 , -(CO) R51 , -(CO) OR51 , -(CO)N( R51 ) 2 , -OR51 , -(C1-C8 alkylene) -OR51 , -( SO2 ) R51 , C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl. R 51 is, independently, hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl; The aforementioned “C3-C8 cycloalkyl”, “heterocyclic”, “aryl” or “C3-C8 cycloalkenyl” is optionally replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R) 2 , -(CS)N(R) 2 , -(SO)R or -( SO2 )R; R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy.
  3. A substituted heterocyclic compound or its salt or oxide according to claim 1 or 2, characterized in that, R4 , R5 , R7 , R8 , R9 , R10 , R11 , R16 , R17 , R18 , R19 , and R20 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, C3-C6 cycloalkenyl, -SF5 , -OR51 , -O-(C1-C6 alkylene) -OR51 , -SR51 , -O-(C1-C6 alkylene) -SR51 , -SOR51 , -( SO2 ) R51 , and -O( SO2 ) R51 , respectively. -N(R 51 ) 2 , -O(CO )R 51 , -O(CS)OR 51 , -O(CS)SR 51 , -N(R 51 )(COR 51 ), -N(R 51 )(COOR 51 ), -N(SO 2 R 51 ) 2 , -(CO)OR 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, triC1-C6 alkylsilyl, -OR 51 , -SR 51 , -SOR 51 , -(SO 2 )R 51 , -N(R 51 ) 2. Replaced by at least one of the groups selected from -O(CO)R 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; X represents C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, -N(R 51 ) 2 , aryl, heterocyclic, aryl-C1-C6 alkyl, or heterocyclic-C1-C6 alkyl; or -N(R 51 ) 2 together to form Among them, the It is either unsubstituted or substituted with at least one group selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl; Y1 and R6 independently represent hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, cyano, -N( R51 ) 2 , -(CO) R51 , -(CO) OR51 , -(CO)N( R51 ) 2 , -OR51 , -(C1-C6 alkylene) -OR51 , -( SO2 ) R51 , C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, aryl-C1-C6 alkyl, or heterocyclic-C1-C6 alkyl. R 51 is, independently, hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, aryl-C1-C6 alkyl, or heterocyclic-C1-C6 alkyl; The aforementioned “C3-C6 cycloalkyl”, “heterocyclic”, “aryl” or “C3-C6 cycloalkenyl” is optionally replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R) 2 , -(CS)N(R) 2 , -(SO)R or -( SO2 )R; R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C6 alkoxy, cyano or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy.
  4. A substituted heterocyclic compound or its salt or oxide according to any one of claims 1-3, characterized in that the compound is selected from any one of Tables 1-2.
  5. A method for preparing a substituted heterocyclic compound or its salt or oxide as described in any one of claims 1-4, characterized by comprising the following steps: (1) When Q represents Q-1 and Q8 represents N, the compound shown in general formula II-1 is reacted with the compound shown in general formula III-1 to obtain the compound shown in general formula I-1. The reaction equation is as follows: (2) When Q represents Q-2 and Q3 represents CH, the compound shown in general formula II-2 is reacted with the compound shown in general formula III-2 to obtain the compound shown in general formula I-2. The reaction equation is as follows: (3) When Q represents Q-2 and Q3 represents N, the salt of the compound shown in general formula II-3 and the salt of the compound shown in formula III-3 (e.g.: The reaction yielded a compound represented by general formula I-3, and the reaction equation is as follows: Wherein, Hal represents halogen, and the definitions of R4, R5 , R6 , R7 , R8 , R16 , R17 , R18 , R20 , Q4 , Q5 , X and Y are as described in any one of claims 1-4; Preferably, reactions (1), (2), and (3) are all carried out in the presence of a solvent; more preferably, a condensing agent is added during reaction (3); even more preferably, the solvent is selected from at least one of aromatic hydrocarbons, DMF, DMA, THF, acetonitrile, dichloroethane, DMSO, dioxane, pyridine, dichloromethane, or ethyl acetate, and/or the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU, or HATU.
  6. [Revised according to Rule 26, 2008.11.2025]
  7. [Revised according to Rule 26, 2008.11.2025]
  8. [Revised according to Rule 26, 2008.11.2025]
  9. [Revised according to Rule 26, 2008.11.2025]
  10. [Revised according to Rule 26, 2008.11.2025] An insecticide composition, characterized in that it comprises an insecticidal effective amount of at least one of the substituted heterocyclic compound or its salt or oxide as described in any one of claims 1-4; preferably, it further comprises a formulation adjuvant; more preferably, it further comprises other active ingredients.
  11. [Revised according to Rule 26, 2008.11.2025] A method for controlling pests, characterized in that it involves exposing the pest or its environment to a biologically effective amount of the substituted heterocyclic compound of any one of claims 1-4, or a salt, oxide, or composition of claim 6.
  12. [Revised according to Rule 26, 2008.11.2025] Use of the substituted heterocyclic compound or its salt, oxide or the composition of claim 6 as described in any one of claims 1-4 in the control of pests.
  13. [Revised according to Rule 26, 2008.11.2025] An intermediate as described in formula II-1, II-2 or II-3 of claim 5.

Description

A substituted heterocyclic compound, its preparation method, insecticidal composition and application Technical Field This invention belongs to the field of pesticide technology, specifically relating to a substituted heterocyclic compound, its preparation method, insecticidal composition, and application. Background Technology In recent years, due to the long-term use of pest control agents, such as insecticides or fungicides, pests have acquired resistance, becoming difficult to control with existing pesticides or fungicides. Furthermore, some known pest control agents are highly toxic, or some damage ecosystems through their long-term persistence. Therefore, despite the large number of known pesticides, there is a need to develop new pest control agents with low toxicity and low residue. Summary of the Invention This invention provides a substituted heterocyclic compound, its preparation method, an insecticidal composition, and its application. The compound exhibits excellent insecticidal activity against fall armyworm, beet armyworm, armyworm, and brown planthopper. The technical solution adopted in this invention is as follows: A substituted heterocyclic compound or its salt or oxide as shown in general formula I: Where Q represents Q3 represents N or CR 11 , Q4 represents N or CR 9 , and Q5 represents N or CR 10 . Q 8 represents N or CR 19 ; R4 , R5 , R7 , R8 , R9 , R10 , R11 , R16 , R17 , R18 , R19 , and R20 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, cycloalkenyl, -SF5 , -OR51 , -O-alkylene- OR51 , -SR51 , -O-alkylene- SR51 , -SOR51 , -( SO2 ) R51 , and -O( SO2 ) R51 , respectively. -N(R 51 ) 2 , -O(CO)R 51 , -O(CS)OR 51 , -O(CS)SR 51 , -N(R 51 )(COR 51 ), -N(R 51 )(COOR 51 ), -N(SO 2 R 51 ) 2 , -(CO)OR 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, trialkylsilyl, -OR 51 , -SR 51 , -SOR 51 , -(SO 2 )R 51 , -N(R 51 ) 2 , -O(CO)R 51 , -O(CO)OR 51 It is substituted by at least one of the groups in -(CO)R 51 or -(CO)N(R 51 ) 2 ; X represents alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cycloalkyl, cycloalkylalkyl, -N(R 51 ) 2 , aryl, heterocyclic, arylalkyl or heterocyclic alkyl; or -N(R 51 ) 2 together to form an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position; Y represents O or NY 1 ; Y1 and R6 independently represent hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cyano, -N( R51 ) 2 , -(CO) R51 , -(CO) OR51 , -(CO)N( R51 ) 2 , -OR51 , -alkylene- OR51 , -( SO2 ) R51 , cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl; R 51 is independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl; The aforementioned “cycloalkyl”, “heterocyclic”, “aryl” or “cycloalkenyl” may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R) 2 , -(CS)N(R) 2 , -(SO)R or -( SO2 )R; R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted with at least one group selected from halogen, hydroxyl, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy. In one specific implementation, R4 , R5 , R7 , R8 , R9 , R10 , R11 , R16 , R17 , R18 , R19 , and R20 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, C3-C8 cycloalkenyl, -SF5 , -OR51 , -O-(C1-C8 alkylene) -OR51 , -SR51 , -O-(C1-C8 alkylene) -SR51 , -SOR51 , -( SO2 ) R51 , and -O( SO2 ) R51 , respectively. -N(R 51 ) 2 , -O(CO )R 51 , -O(CS)OR 51 , -O(CS)SR 51 , -N(R 51 )(COR 51 ), -N(R 51 )(COOR 51 ), -N(SO 2 R 51 ) 2 , -(CO)OR 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, triC1-C8 alkylsilyl, -OR 51 , -SR 51 , -SOR 51 , -(SO 2 )R 51 , -N(R 51 ) 2. Replaced by at least one of the groups selected from -O(CO)R 51 , -O(CO)OR 51 , -(CO)R 51 or -(CO)N(R 51 ) 2 ; X represents C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, -N(R 51 ) 2 , aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl; or -N(R 51 ) 2 together to form Among them, the It is either unsubstituted or substituted with at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl; Y1 and R6 independently re